Pyrazole compound

ABSTRACT

A pyrazole compound of formula (a): 
                         
wherein R 1  represents C1-C4 alkyl or trifluoromethyl, R 2  represents C1-C4 alkyl, R 3  represents hydrogen or C1-C6 alkyl; R 4  represents halogen and so on, m represents 0 to 4 integer; R 5  represents halogen and so on, n represents 0 to 4 integer; R 6  and R 7  are same or different and represents hydrogen, halogen or methyl; X represents oxygen or R 8 O—N; R 8  represents hydrogen, C1-C6 alkyl and the like;
 
has an excellent controlling activity against noxious arthropods.

TECHNICAL FIELD

The present invention relates to pyrazole compounds, intermediatecompounds thereof and a control method of noxious arthropods by usingthem.

BACKGROUND ART

A certain type of pyrazole compounds is known as an active ingredient ofpesticides and acaricides. See U.S. Pat. No. 4,843,068.

However, noxious arthropods controlling activity of these pyrazolecompounds is not enough in some cases, and therefore a novel compoundhaving a noxious arthropods controlling activity is desired.

DISCLOSURE OF INVENTION

The present invention provides a pyrazole compound (hereinafter,referred as the compound of the present invention) of formula (a):

wherein R¹ represents C1-C4 alkyl or trifluoromethyl, R² representsC1-C4 alkyl, R³ represents hydrogen or C1-C6 alkyl; R⁴ representshalogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl or C1-C3 haloalkoxy,m represents 0 to 4 integer, each of R⁴s is same or different when m is2 to 4 integer; R⁵ represents halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3haloalkyl or C1-C3 haloalkoxy, n represents 0 to 4 integer, each of R⁵sis same or different when n is 2 to 4 integer; R⁶ and R⁷ are same ordifferent and represents hydrogen, halogen or methyl, X representsoxygen or R⁸O—N; R⁸ represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl,C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl,C2-C5 cyano alkyl or benzyl (wherein the benzyl may be substituted withhalogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl,trifluoromethyl or trifluoromethoxy);

-   a noxious arthropods controlling composition comprising the compound    of the present invention; and a method for controlling noxious    arthropods characterized by applying an effective amount of the    compound of the present invention to noxious arthropods or habitat    of noxious arthropods.

Furthermore, the present invention also provides a compound of formula(b):

wherein R¹ represents C1-C4 alkyl or trifluoromethyl, R² representsC1-C4 alkyl, R³ represents hydrogen or C1-C6 alkyl; R⁴ representshalogen, C1-C3 alkyl, C1-C3 alkoxy or trifluoromethyl, m represents 0 to4 integer, each of R⁴s is same or different when m is 2 to 4 integer; R⁵represents halogen, C1-C3 alkyl, C1-C3 alkoxy or trifluoromethyl, nrepresents 0 to 4 integer, each of R⁵s is same or different when n is 2to 4 integer; X represents oxygen or by R⁸O—N; R⁸ represents hydrogen,C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or benzyl (wherein thebenzyl may be substituted with halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C5alkoxycarbonyl, trifluoromethyl or trifluoro methoxy); which is usefulas an intermediate of the compound of the present invention.

In the compound of the present invention, each substituent representedby R¹, R², R³, R⁴, R⁵, R⁶, R⁷ or R⁸ is exemplified the followingsubstituents concretely.

The C1-C4 alkyl represented by R¹ is methyl, ethyl, propyl, isopropyl,butyl, isobutyl, sec-butyl and tert-butyl.

The C1-C4 alkyl represented by R² is methyl, ethyl, propyl, isopropyl,butyl, isobutyl, sec-butyl and tert-butyl.

The C1-C6 alkyl represented by R³ includes methyl, ethyl, propyl,isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,3-methylbutyl, 2,2-dimethylpropyl, 1,1-dimethylpropyl, 1-ethylpropyl,hexyl, 5-methylpentyl, 2-ethylbutyl, 3-methylpentyl and1,3-dimethylbutyl.

The halogen represented by R⁴ and R⁵ is a fluorine, chlorine, bromineand iodine;

-   the C1-C3 alkyl includes methyl, ethyl, propyl and isopropyl;-   the C1-C3 alkoxy includes methoxy, ethoxy, propoxy and isopropoxy;-   the C1-C3 haloalkyl includes trifluoromethyl, 2-fluoroethyl,    2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 2-chloroethyl and    3-bromopropyl;-   the C1-C3 haloalkoxy includes trifluoroalkoxy, 2,2,2-trifluoroethoxy    and 3,3,3-trifluoropropoxy.

The halogen represented by R⁶ is a fluorine, chlorine, bromine andiodine.

The halogen represented by R⁷ is a fluorine, chlorine, bromine andiodine.

The C1-C6 alkyl represented by R⁸ includes methyl, ethyl, propyl,isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl,tert-pentyl,

-   1-methylbutyl, 1,2-dimethylpropyl and hexyl;-   the C1-C6 haloalkyl includes fluoromethyl, 2-fluoroethyl,    2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl,    5,5,5-trifluoropentyl, 2-chloroethyl, 3-chloropropyl, 3-bromopropyl,    4-chlorobutyl, 4-bromobutyl, 4-chloropentyl and 4-bromopentyl;-   the C3-C6 alkenyl includes allyl, 2-methyl-2-propenyl,    3-methyl-2-butenyl, 2-butenyl, 3-butenyl, 2-pentenyl, 3-pentenyl,    2-hexenyl and 3-hexenyl;-   the C3-C6 haloalkenyl includes 3-chloro-2-propenyl,    3,3-dichloro-2-propenyl, 3-bromo-2-propenyl, 3,3-dibromo-2-propenyl,    2-chloro-2-propenyl, 2-bromo-2-propenyl, 2-fluoro-2-propenyl,    2,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 3-chloro-2-butenyl,    3-chloro-4,4,4-trifluoro-2-butenyl, 4-chloro-2-butenyl, butenyl,    4-bromo-2-butenyl and 2,3,3-trifluoro-2-propenyl;-   the C3-C6 alkynyl includes 2-propynyl, 2-butynyl, 2-pentynyl,    3-butynyl and 1-methyl-2-propynyl;-   the C3-C6 haloalkynyl includes 3-chloro-2-propynyl,    4-chloro-3-butynyl, 5-chloro-4-pentynyl, 6-chloro-5-hexynyl,    3-bromo-2-propynyl, 4-bromo-3-butynyl, 5-bromo-4-pentynyl and    6-bromo-5-hexynyl;-   the C2-C5 cyano alkyl includes cyanomethyl, 2-cyanoethyl,    3-cyanopropyl and 4-cyanobutyl;-   the benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C4    alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoromethoxy    includes benzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl,    2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-bromobenzyl,    3-bromobenzyl, 4-bromobenzyl, 2,3-dichlorobenzyl,    3,5-dichlorobenzyl, 2,4-dichlorobenzyl, 2-methylbenzyl,    3-methylbenzyl, 4-methylbenzyl, 2,3-dimethylbenzyl,    3,5-dimethylbenzyl, 2,4-dimethylbenzyl, 2-methoxybenzyl,    3-methoxybenzyl, 4-methoxybenzyl, 2,3-dimethoxybenzyl,    3,5-dimethoxybenzyl, 2,4-dimethoxybenzyl, 4-methoxycarbonylbenzyl,    4-ethoxycarbonylbenzyl, 4-propoxycarbonylbenzyl,    4-trifluoromethylbenzyl and 4-trifluoromethoxybenzyl.

The embodiments of the compound of the present invention are exemplifiedas follows:

-   the pyrazole compound wherein R¹ is methyl in the formula (a);-   the pyrazole compound wherein R¹ is ethyl in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl in the formula    (a);-   the pyrazole compound wherein R² is methyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen in the formula (a);-   the pyrazole compound wherein R³ is methyl in the formula (a);-   the pyrazole compound wherein m is 0 in the formula (a);-   the pyrazole compound wherein n is 0 in the formula (a);-   the pyrazole compound wherein R⁶ is chlorine in the formula (a);-   the pyrazole compound wherein R⁶ and R⁷ are chlorine in the formula    (a);-   the pyrazole compound wherein R¹ is methyl, and R² is methyl in the    formula (a);-   the pyrazole compound wherein R¹ is ethyl, and R² is methyl in the    formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, and R² is    methyl in the formula (a);-   the pyrazole compound wherein R¹ is methyl, and R⁶ is chlorine in    the formula (a);-   the pyrazole compound wherein R¹ is ethyl, and R⁶ is chlorine in the    formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, and R⁶ is    chlorine in the formula (a);-   the pyrazole compound wherein R¹ is methyl, and R⁶ and R⁷ are    chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, and R⁶ and R⁷ are    chlorine in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, and R⁶ and R⁷    are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is methyl, R² is methyl, and R⁶ is    chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, and R⁶ is    chlorine in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, R² is methyl,    and R⁶ is chlorine in the formula (a);-   the pyrazole compound wherein R¹ is methyl, R² is methyl, and R⁶ and    R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, and R⁶ and    R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, R² is methyl,    and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is methyl, R² is methyl, R³ is    hydrogen, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, R³ is    hydrogen atom, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, R² is methyl,    R³ is hydrogen atom, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is methyl, R² is methyl, R³ is    methyl, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, R³ is    methyl, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, R² is methyl,    R³ is methyl, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is methyl, R² is methyl, m is 0,    and n is 0 in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, m is 0, and    n is 0 in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, R² is methyl, m    is 0, and n is 0 in the formula (a);-   the pyrazole compound wherein R¹ is methyl, R² is methyl, m is 0, n    is 0, and R⁶ is chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, m is 0, n    is 0, and R⁶ is chlorine in the formula (a);-   the pyrazole compound wherein R¹ is trifluoromethyl, R² is methyl, m    is 0, n is 0, and R⁶ is chlorine in the formula (a);-   the pyrazole compound wherein R² is methyl, and R⁶ is chlorine in    the formula (a);-   the pyrazole compound wherein R² is methyl, and R⁶ and R⁷ are    chlorine in the formula (a);-   the pyrazole compound wherein R² is methyl, m is 0, and n is 0 in    the formula (a);-   the pyrazole compound wherein R² is methyl, m is 0, n is 0, and R⁶    is chlorine in the formula (a);-   the pyrazole compound wherein R² is methyl, m is 0, n is 0, and R⁶    and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein m is 0, and n is 0 in the formula (a);-   the pyrazole compound wherein m is 0, n is 0, and R⁶ is chlorine in    the formula (a);-   the pyrazole compound wherein m is 0, and n is 0, and R⁶ and R⁷ are    chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen in the formula (a);-   the pyrazole compound wherein R³ is C1-C6 alkyl in the formula (a);-   the pyrazole compound wherein X is R⁸O—N; R⁸ is hydrogen, C1-C6    alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6    alkynyl, C3-C6 haloalkynyl, C2-C5 cyanoalkyl or benzyl (wherein the    benzyl may be substituted with halogen, C1-C4 alkyl, C1-C4 alkoxy,    C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoromethoxy) in the    formula (a);-   the pyrazole compound wherein X is R⁸O—N, and R⁸ is hydrogen, C1-C6    alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6    alkynyl, C3-C6 haloalkynyl or C2-C5 cyanoalkyl in the formula (a);-   the pyrazole compound wherein X is R⁸O—N, and R⁸ is benzyl (wherein    the benzyl may be substituted with halogen, C1-C4 alkyl, C1-C4    alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoromethoxy)    in the formula (a);-   the pyrazole compound wherein X is oxygen in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, and R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyanoalkyl or    benzyl (wherein the benzyl may be substituted with halogen, C1-C4    alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or    trifluoromethoxy) in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, and R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl or C2-C5 cyanoalkyl in    the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, and R⁸ is    benzyl (wherein the benzyl may be substituted with halogen, C1-C4    alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or    trifluoromethoxy) in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, and X is oxygen in the    formula (a);-   the pyrazole compound wherein R³ is a hydrogen atom, X is R⁸O—N, R⁸    is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyanoalkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or    trifluoromethoxy), R⁴ and R⁵ are halogen, C1-C3 alkyl, C1-C3 alkoxy    or trifluoromethyl, and m and n are 0 to 2 integer in the formula    (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl or C2-C5 cyanoalkyl,    R⁴ and R⁵ are halogen, C1-C3 alkyl, C1-C3 alkoxy or trifluoromethyl,    and m and n are 0 to 2 integer in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or    trifluoromethoxy), R⁴ and R⁵ are halogen, C1-C3 alkyl, C1-C3 alkoxy    or trifluoromethyl, and m and n are 0 to 2 integer in the formula    (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, and R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl or C2-C5 cyanoalkyl,    and R⁴ and R⁵ are hydrogen in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is oxygen, and R⁴    and R⁵ are halogen, C1-C3 alkyl, C1-C3 alkoxy or trifluoromethyl, m    and n are 0 to 2 integer in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ is halogen, X is    R⁸O—N, and R⁸ is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6    alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5    cyanoalkyl or benzyl (the benzyl may be substituted with halogen,    C1-C4 alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or    trifluoromethoxy) in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ is halogen, X is    R⁸O—N, and R⁸ is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6    alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl or    C2-C5 cyanoalkyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ is halogen, X is    R⁸O—N, and R⁸ is benzyl (the benzyl may be substituted with halogen,    C1-C4 alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or    trifluoromethoxy) in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ is halogen, and X    is oxygen in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ and R⁷ are halogen,    X is R⁸O—N, and R⁸ is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6    alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5    cyanoalkyl or benzyl (the benzyl may be substituted with halogen,    C1-C4 alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or    trifluoro methoxy) in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ and R⁷ are halogen,    X is R⁸O—N, and R⁸ is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6    alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl or    C2-C5 cyanoalkyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ and R⁷ are halogen,    X is R⁸O—N, and R⁸ is benzyl (the benzyl may be substituted with    halogen, a C1-C4 alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl,    trifluoromethyl or trifluoro methoxy) in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, R⁶ and R⁷ are halogen,    and X is oxygen in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R¹ is methyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R¹ is ethyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R¹ is trifluoromethyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, a C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R² is methyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R³ is hydrogen in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R³ is methyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and m is 0 in the formula (a);-   the pyrazole compound wherein n is 0 in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R⁶ is chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, a C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), R¹ is methyl, and R² is methyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), R¹ is ethyl, and R² is methyl in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano-alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), R¹ is trifluoromethyl, and R² is methyl in the formula    (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), R¹ is methyl, R² is methyl, R³ is hydrogen, and R⁶ and R⁷    are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, R³ is    hydrogen, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), R¹ is trifluoromethyl, R² is methyl, R³ is hydrogen, and    R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), R¹ is methyl, R² is methyl, R³ is methyl, and R⁶ and R⁷    are chlorine in the formula (a);-   the pyrazole compound wherein R¹ is ethyl, R² is methyl, R³ is    methyl, and R⁶ and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), R¹ is trifluoromethyl, R² is methyl, R³ is methyl, and R⁶    and R⁷ are chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), m is 0, and n is 0 in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), m is 0, n is 0, and R⁶ is chlorine in the formula (a);-   the pyrazole compound wherein R³ is hydrogen, X is R⁸O—N, R⁸ is    hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6    haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5 cyano alkyl or    benzyl (the benzyl may be substituted with halogen, C1-C4 alkyl,    C1-C4 alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro    methoxy), m is 0, n is 0, and R⁶ and R⁷ are chlorine in the formula    (a).

The compound of the present invention can be produced by the followingmethod such as Production Method 1 to Production Method 4.

Production Method 1

The compound of the present invention is produced by making a compoundof formula (b):

wherein R¹, R², R³, R⁴, R⁵, X, m and n have the same meaning asdescribed above;

-   react with a compound of formula (e):    L—CH₂CH═C(R⁶)(R⁷)  (e)    wherein R⁶ and R⁷ have the same meaning as described above, and L    represents halogen (such as chlorine or bromine),    methanesulfonyloxy, benzensulfonyloxy or toluenesulfonyloxy.

The reaction is carried out in the presence of a base usually in asolvent. The reaction temperature is usually −78 to 150° C., and thereaction period is 0.1 to 24 hours.

Examples of the solvent used for the reaction include ketones such asacetone, methyl ethyl ketone and so on; aromatic hydrocarbons such astoluene, xylene and so on; aliphatic hydrocarbons such as hexane,heptane and so on; ethers such as diethyl ether, tetrahydrofuran,1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane and so on;halogenated hydrocarbons such as dichloromethane, chloroform,1,2-dichloroethane, chlorobenzene, dichlorobenzene and so on; amidessuch as N,N-dimethylformamide, N,N-diethylacetamide and so on; nitritessuch as acetonitrile and so on; dimethylsulfoxide; and the mixturethereof.

Examples of the base used for the reaction include inorganic base suchas hydroxides of alkali metal or alkaline earth metal (for examplesodium hydroxide, potassium hydroxide, calcium hydroxide and so on),hydrides of alkali metal or alkaline earth metal (for example sodiumhydride, potassium hydride, calcium hydride and so on), sodiumcarbonate, potassium carbonate and so on; and organic base such astriethylamine and so on.

Based on one mole of the compound of the formula (b), 1 to 3 mole of thecompound of formula (e) and 1 to 3 mole of the base are usually used.

After the reaction, the reaction mixture is poured into water, extractedwith an organic solvent, the organic layer is dried and concentrated togive the compound of the present invention. Further, it is possible topurify the obtained the compound of the present invention bychromatography, recrystallization and so on.

Production Method 2

The compound of the present invention, wherein X is R⁸O—N in the formula(a), is produced by making a compound of formula (c):

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, X, m and n have the same meaning asdescribed above;

-   react with a hydroxyl amine compound of formula (d):    R⁸O—NH₂  (d)    wherein R⁸ has the same meaning as described above;-   itself or the salt thereof, such as hydrochloric acid salt, sulfuric    acid salt, nitric acid salt and so on.

The reaction is carried out in the presence of a base usually in asolvent. The reaction temperature is usually −78 to 150° C., and thereaction period is 0.1 to 24 hours.

Examples of the solvent used for the reaction include alcohol such asmethanol, ethanol and so on; aromatic hydrocarbons such as benzene,toluene, xylene and so on; aliphatic hydrocarbons such as hexane,heptane and so on; ethers such as diethyl ether, tetrahydrofuran,1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane and so on;halogenated hydrocarbons such as dichloromethane, chloroform,1,2-dichloroethane, chlorobenzene, dichlorobenzene and so on; amidessuch as N,N-dimethylformamide, N,N-diethylacetamide and so on;dimethylsulfoxide; water and the mixture thereof.

Examples of the base used for the reaction include inorganic base suchas hydrides of alkali metal or alkaline earth metal (for example sodiumhydride, potassium hydride, calcium hydride and so on), sodiumcarbonate, potassium carbonate and so on; and organic base such astriethylamine, pyridine and so on.

When excess of hydroxylamine compound of formula (d) itself is used, thebase may not be needed.

Based on one mole of the compound of the formula (c), 1 to 3 mole of thehydroxyl amine compound of formula (d) itself or the acid thereof and 1to 10 mole of the base are usually used.

After the reaction, the reaction mixture is poured into water, extractedwith an organic solvent, the organic layer is dried and concentrated togive the compound of the present invention wherein X is R⁸O—N in theformula (a). Further, it is possible to purify the obtained the compoundof the present invention by chromatography, recrystallization and so on.

Production Method 3

The compound of the present invention, wherein X is R⁸O—N in the formula(a), is produced by making a compound of formula (f):

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, m and n have the same meaning asdescribed above;

-   react with a compound of formula (g):    L-R⁸  (g)    wherein R⁸ has the same meaning as described above and L represents    halogen (such as chlorine or bromine), methanesulfonyloxy,    benzensulfonyloxy or toluenesulfonyloxy.

The reaction is carried out in the presence of a base usually in asolvent. The reaction temperature is usually −78 to 150° C., and thereaction period is 0.1 to 24 hours.

Examples of the solvent used for the reaction include ketones such asacetone, methyl ethyl ketone and so on; aromatic hydrocarbons such asbenzene, toluene, xylene and so on; aliphatic hydrocarbons such ashexane, heptane and so on; ethers such as diethyl ether,tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethaneand so on; halogenated hydrocarbons such as chlorobenzene,dichlorobenzene and so on; amides such as N,N-dimethylformamide,N,N-diethylacetamide and so on; nitrites such as acetonitrile and so on;dimethylsulfoxide; and the mixture thereof.

Examples of the base used for the reaction include inorganic base suchas hydroxides of alkali metal or alkaline earth metal (for examplesodium hydroxide, potassium hydroxide, calcium hydroxide and so on),hydrides of alkali metal or alkaline earth metal (for example sodiumhydride, potassium hydride, calcium hydride and so on), sodiumcarbonate, potassium carbonate and so on; and organic base such astriethylamine.

Based on one mole of the compound of the formula (f), 1 to 1.5 mole ofthe compound of formula (g) and 1 to 1.2 mole of the base are usuallyused.

After the reaction, the reaction mixture is poured into water, extractedwith an organic solvent, the organic layer is dried and concentrated togive an objective compound wherein X is R⁸O—N in the formula (a).Further, it is possible to purify the obtained the compound of thepresent invention by chromatography, recrystallization and so on.

Production Method 4

The compound of the present invention, wherein X is oxygen in theformula (a), is produced by making the compound of formula (h):

wherein R¹, R² and R³ have the same meaning as described above;

-   react with a compound of formula (k):

wherein R⁴, R⁵, R⁶, R⁷, m and n have the same meaning as describedabove.

The reaction is carried out in the presence of a base usually in asolvent. The reaction temperature is usually −78 to 150° C., and thereaction period is 0.1 to 24 hours.

Examples of the solvent used for the reaction include aromatichydrocarbons such as toluene, xylene and so on; aliphatic hydrocarbonssuch as hexane, heptane and so on; ethers such as diethyl ether,tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethaneand so on; amides such as N,N-dimethylformamide, N,N-diethylacetamideand so on; dimethylsulfoxide; and the mixture thereof.

Examples of the base used for the reaction include inorganic base suchas hydroxides of alkali metal or alkaline earth metal (for examplesodium hydroxide, potassium hydroxide, calcium hydroxide and so on),hydrides of alkali metal or alkaline earth metal (for example sodiumhydride, potassium hydride, calcium hydride and so on), sodiumcarbonate, potassium carbonate and so on; and organic base such astriethylamine and so on.

Based on one mole of the compound of the formula (h), 0.5 to 3 mole ofthe compound of formula (k) and 1 to 3 mole of the base are usuallyused.

After the reaction, the reaction mixture is poured into water, extractedwith an organic solvent, the organic layer is dried, and concentrated togive the compound of the present invention wherein X is oxygen in theformula (a). Further, it is possible to purify the obtained the compoundof the present invention by chromatography, recrystallization and so on.

Next, the methods of producing the intermediates of the presentinvention are described following.

The compound of formula (b-2):

wherein R¹, R², R³, R⁴, R⁵, R⁸, m and n have the same meaning asdescribed above;

-   for example, can be produced by making a compound of formula (b-1):

wherein R¹, R², R³, R⁴, R⁵, m and n have the same meaning as describedabove;

-   react with the hydroxyl amine compound of formula (d) itself or the    salt thereof, such as hydrochloric acid salt, sulfuric acid salt,    nitric acid salt and so on.

The reaction is carried out in the presence of a base usually in asolvent. The reaction temperature is usually −78 to 150° C., and thereaction period is 0.1 to 24 hours.

Examples of the solvent used for the reaction include alcohol such asmethanol, ethanol and so on; aromatic hydrocarbons such as benzene,toluene, xylene and so on; aliphatic hydrocarbons such as hexane,heptane and so on; ethers such as diethyl ether, tetrahydrofuran,1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane and so on;halogenated hydrocarbons such as dichloromethane, chloroform,1,2-dichloroethane, chlorobenzene, dichlorobenzene and so on; amidessuch as N,N-dimethylformamide, N,N-diethylacetamide and so on;dimethylsulfoxide; water and the mixture thereof.

Examples of the base used for the reaction include inorganic base suchas hydroxides of alkali metal or alkaline earth metal (for examplesodium hydroxide, potassium hydroxide, calcium hydroxide and so on),hydrides of alkali metal or alkaline earth metal (for example sodiumhydride, potassium hydride, calcium hydride and so on), sodiumcarbonate, potassium carbonate and so on; and organic base such astriethylamine and so on. When excess of the hydroxyl amine compound offormula (d) itself is used, the base may not be needed. Based on onemole of the compound of the formula (b-1), 1 to 3 mole of the hydroxylamine compound of formula (d) itself or the salt thereof and 1 to 10mole of the base are usually used.

After the reaction, the reaction mixture is poured into water, extractedwith an organic solvent, the organic layer is dried and concentrated togive the compound of formula (b-2). Further, it is possible to purifythe obtained the compound of formula (b-2) by chromatography,recrystallization and so on.

The compound of formula (b-1), for example, can be produced by making athe compound of formula (h) react with a compound of formula (i):

wherein R⁴, R⁵, m and n have the same meaning as described above.

The reaction is carried out in the presence of a base usually in asolvent. The reaction temperature is usually −78 to 150° C., and thereaction period is 0.1 to 24 hours.

Examples of the solvent used for the reaction include aromatichydrocarbons such as toluene, xylene and so on; aliphatic hydrocarbonssuch as hexane, heptane and so on; ethers such as diethyl ether,tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethaneand so on; amides such as N,N-dimethylformamide, N,N-diethylacetamideand so on; dimethylsulfoxide; and the mixture thereof.

Examples of the base used for the reaction include inorganic base suchas hydroxides of alkali metal or alkaline earth metal (for examplesodium hydroxide, potassium hydroxide, calcium hydroxide and so on),hydrides of alkali metal or alkaline earth metal (for example sodiumhydride, potassium hydride, calcium hydride and so on), sodiumcarbonate, potassium carbonate and so on; and organic base such astriethylamine and so on.

Based on one mole of the compound of the formula (h), 0.5 to 3 mole ofthe compound of formula (i) and 1 to 3 mole of the base are usuallyused.

After the reaction, the reaction mixture is poured into water, extractedwith an organic solvent, the organic layer is dried and concentrated togive the compound of formula (b-1). Further, it is possible to purifythe obtained the compound of formula (b-1) by chromatography,recrystallization and so on.

The compound of formula (b-1) can be produced by protecting one of thetwo phenolic hydroxy groups in the compound of formula (i) with anappropriate protecting group (such as benzyl, tert butyldimethylsilyland methoxymethyl), subjecting with the reaction described above, andremoving the protecting group.

The compounds of the present invention are exemplified below.

Each of R¹, R² and X in the formula (I) to (XXXXXIII) is any one of thecombination described in Table 1 or Table 2.

TABLE 1 (X represents R⁸O—N) R¹ R² R⁸ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃CH₂ CH₃ CH₃CH₃CH₂CH₂ CH₃ CH₃ (CH₃)₂CH CH₃ CH₃ CH₃CH₂CH₂CH₂ CH₃ CH₃ CH₃CH₂—(CH₃)CHCH₃ CH₃ (CH₃)₂CH—CH₂ CH₃ CH₃ (CH₃)₃C CH₃ CH₃ CH₃CH₂CH₂CH₂CH₂ CH₃ CH₃(CH₃)₂CH—CH₂CH₂ CH₃ CH₃ (CH₃)₃C—CH₂ CH₃ CH₃ CH₃CH₂CH₂—(CH₃)CH CH₃ CH₃(CH₃)₂CH—(CH₃)CH CH₃ CH₃ CH₃CH₂CH₂CH₂CH₂CH₂ CH₃ CH₃ CH₂F CH₃ CH₃CH₂F—CH₂ CH₃ CH₃ CF₃CH₂ CH₃ CH₃ CF₃CH₂CH₂ CH₃ CH₃ CF₃CH₂CH₂CH₂ CH₃ CH₃CF₃CH₂CH₂CH₂CH₂ CH₃ CH₃ CH₂Cl—CH₂CH₂ CH₃ CH₃ CH₂Br—CH₂CH₂ CH₃ CH₃CH₂Cl—CH₂CH₂CH₂ CH₃ CH₃ CH₂Br—CH₂CH₂CH₂ CH₃ CH₃ CH₂Cl—CH₂CH₂CH₂CH₂ CH₃CH₃ CH₂Br—CH₂CH₂CH₂CH₂ CH₃ CH₃ CH₂═CHCH₂ CH₃ CH₃ CH₂═C(CH₃)—CH₂ CH₃ CH₃(CH₃)₂C═CHCH₂ CH₃ CH₃ CH₃CH═CHCH₂ CH₃ CH₃ CH₂═CHCH₂CH₂ CH₃ CH₃CH₃CH₂CH═CHCH₂ CH₃ CH₃ CH₃CH═CHCH₂CH₂ CH₃ CH₃ CH₃CH₂CH₂CH═CHCH₂ CH₃ CH₃CH₃CH₂CH═CHCH₂CH₂ CH₃ CH₃ CHCl═CHCH₂ CH₃ CH₃ CCl₂═CHCH₂ CH₃ CH₃CHBr═CHCH₂ CH₃ CH₃ CBr₂═CHCH₂ CH₃ CH₃ CH₂═CClCH₂ CH₃ CH₃ CH₂═CBrCH₂ CH₃CH₃ CH₂═CFCH₂ CH₃ CH₃ CHCl═CClCH₂ CH₃ CH₃ CHBr═CBrCH₂ CH₃ CH₃CH₃CCl═CHCH₂ CH₃ CH₃ CF₃CCl═CHCH₂ CH₃ CH₃ CClH₂—CH═CHCH₂ CH₃ CH₃CBrH₂—CH═CHCH₂ CH₃ CH₃ CF₂═CFCH₂ CH₃ CH₃ CH≡CCH₂ CH₃ CH₃ CH₃C≡CCH₂ CH₃CH₃ CH₃CH₂C≡CCH₂ CH₃ CH₃ CH₃C≡CCH₂CH₂ CH₃ CH₃ CH≡C—(CH₃)CH CH₃ CH₃N≡CCH₂ CH₃ CH₃ N≡CCH₂CH₂ CH₃ CH₃ N≡CCH₂CH₂CH₂ CH₃ CH₃ N≡CCH₂CH₂CH₂CH₂CH₃ CH₃ H CH₃ CH₃ C₆H₅—CH₂ CH₃ CH₃ 2-F—C₆H₄—CH₂ CH₃ CH₃ 3-F—C₆H₄—CH₂ CH₃CH₃ 4-F—C₆H₄—CH₂ CH₃ CH₃ 2-Cl—C₆H₄—CH₂ CH₃ CH₃ 3-Cl—C₆H₄—CH₂ CH₃ CH₃4-Cl—C₆H₄—CH₂ CH₃ CH₃ 2-Br—C₆H₄—CH₂ CH₃ CH₃ 3-Br—C₆H₄—CH₂ CH₃ CH₃4-Br—C₆H₄—CH₂ CH₃ CH₃ 4-I—C₆H₄—CH₂ CH₃ CH₃ 2-CH₃—C₆H₄—CH₂ CH₃ CH₃3-CH₃—C₆H₄—CH₂ CH₃ CH₃ 4-CH₃—C₆H₄—CH₂ CH₃ CH₃ 4-CF₃—C₆H₄—CH₂ CH₃ CH₃4-CH₃CH₂—C₆H₄—CH₂ CH₃ CH₃ 4-(CH₃)₂CH—C₆H₄—CH₂ CH₃ CH₃4-CH₃CH₂CH₂—C₆H₄—CH₂ CH₃ CH₃ 4-(CH₃)₃C—C₆H₄—CH₂ CH₃ CH₃2,4-(CH₃)₂—C₆H₃—CH₂ CH₃ CH₃ 2,4,6-(CH₃)₃—C₆H₂—CH₂ CH₃ CH₃2,4-Cl₂—C₆H₃—CH₂ CH₃ CH₃ 3,4-Cl₂—C₆H₃—CH₂ CH₃ CH₃ 2,5-Cl₂—C₆H₃—CH₂ CH₃CH₃ 3,5-Cl₂—C₆H₃—CH₂ CH₃ CH₃ 2,6-Cl₂—C₆H₃—CH₂ CH₃ CH₃ 4-CH₃O—C₆H₄—CH₂CH₃ CH₃ 4-CF₃O—C₆H₄—CH₂ CH₃ CH₃ 4-CH₃CH₂O—C₆H₄—CH₂ CH₃ CH₃4-(CH₃)₂CHO—C₆H₄—CH₂ CH₃ CH₃ 4-(CH₃)₃CO—C₆H₄—CH₂ CH₃ CH₃4-CH₃OC(═O)—C₆H₄—CH₂ CH₃ CH₃ 4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CH₃ CH₃4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CH₃ CH₃ 4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CH₃ CH₃4-(CH₃)₃COC(═O)—C₆H₄—CH₂ CH₃ CH₃ CH₂Cl—CH₂ CH₃ CH₃ CCl≡CCH₂ CH₃ CH₃CBr≡CCH₂ CH₃ CH₃CH₂ CH₃ CH₃ CH₃CH₂ CH₃CH₂ CH₃ CH₃CH₂ CH₃CH₂CH₂ CH₃CH₃CH₂ (CH₃)₂CH CH₃ CH₃CH₂ CH₃CH₂CH₂CH₂ CH₃ CH₃CH₂ CH₃CH₂—(CH₃)CH CH₃CH₃CH₂ (CH₃)₂CHCH₂ CH₃ CH₃CH₂ (CH₃)₃C CH₃ CH₃CH₂ CH₃CH₂CH₂CH₂CH₂ CH₃CH₃CH₂ (CH₃)₂CHCH₂CH₂ CH₃ CH₃CH₂ (CH₃)₃CCH₂ CH₃ CH₃CH₂ CH₃CH₂CH₂—(CH₃)CHCH₃ CH₃CH₂ (CH₃)₂CH—(CH₃)CH CH₃ CH₃CH₂ CH₃CH₂CH₂CH₂CH₂CH₂ CH₃ CH₃CH₂CH₂F CH₃ CH₃CH₂ CH₂F—CH₂ CH₃ CH₃CH₂ CF₃CH₂ CH₃ CH₃CH₂ CF₃CH₂CH₂ CH₃CH₃CH₂ CF₃CH₂CH₂CH₂ CH₃ CH₃CH₂ CF₃CH₂CH₂CH₂CH₂ CH₃ CH₃CH₂ CH₂Cl—CH₂CH₂CH₃ CH₃CH₂ CH₂Br—CH₂CH₂ CH₃ CH₃CH₂ CH₂Cl—CH₂CH₂CH₂ CH₃ CH₃CH₂CH₂Br—CH₂CH₂CH₂ CH₃ CH₃CH₂ CH₂Cl—CH₂CH₂CH₂CH₂ CH₃ CH₃CH₂CH₂Br—CH₂CH₂CH₂CH₂ CH₃ CH₃CH₂ CH₂═CHCH₂ CH₃ CH₃CH₂ CH₂═C(CH₃)—CH₂ CH₃CH₃CH₂ (CH₃)₂C═CHCH₂ CH₃ CH₃CH₂ CH₃CH═CHCH₂ CH₃ CH₃CH₂ CH₂═CHCH₂CH₂ CH₃CH₃CH₂ CH₃CH₂CH═CHCH₂ CH₃ CH₃CH₂ CH₃CH═CHCH₂CH₂ CH₃ CH₃CH₂CH₃CH₂CH₂CH═CHCH₂ CH₃ CH₃CH₂ CH₃CH₂CH═CHCH₂CH₂ CH₃ CH₃CH₂ CHCl═CHCH₂ CH₃CH₃CH₂ CCl₂═CHCH₂ CH₃ CH₃CH₂ CHBr═CHCH₂ CH₃ CH₃CH₂ CBr₂═CHCH₂ CH₃ CH₃CH₂CH₂═CClCH₂ CH₃ CH₃CH₂ CH₂═CBrCH₂ CH₃ CH₃CH₂ CH₂═CFCH₂ CH₃ CH₃CH₂CHCl═CClCH₂ CH₃ CH₃CH₂ CHBr═CBrCH₂ CH₃ CH₃CH₂ CH₃CCl═CHCH₂ CH₃ CH₃CH₂CF₃CCl═CHCH₂ CH₃ CH₃CH₂ CClH₂—CH═CHCH₂ CH₃ CH₃CH₂ CBrH₂—CH═CHCH₂ CH₃CH₃CH₂ CF₂═CFCH₂ CH₃ CH₃CH₂ CH≡CCH₂ CH₃ CH₃CH₂ CH₃C≡CCH₂ CH₃ CH₃CH₂CH₃CH₂C≡CCH₂ CH₃ CH₃CH₂ CH₃C≡CCH₂CH₂ CH₃ CH₃CH₂ CH≡C—(CH₃)CH CH₃ CH₃CH₂N≡CCH₂ CH₃ CH₃CH₂ N≡CCH₂CH₂ CH₃ CH₃CH₂ N≡CCH₂CH₂CH₂ CH₃ CH₃CH₂N≡CCH₂CH₂CH₂CH₂ CH₃ CH₃CH₂ H CH₃ CH₃CH₂ C₆H₅—CH₂ CH₃ CH₃CH₂ 2-F—C₆H₄—CH₂CH₃ CH₃CH₂ 3-F—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-F—C₆H₄—CH₂ CH₃ CH₃CH₂ 2-Cl—C₆H₄—CH₂CH₃ CH₃CH₂ 3-Cl—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-Cl—C₆H₄—CH₂ CH₃ CH₃CH₂2-Br—C₆H₄—CH₂ CH₃ CH₃CH₂ 3-Br—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-Br—C₆H₄—CH₂ CH₃CH₃CH₂ 4-I—C₆H₄—CH₂ CH₃ CH₃CH₂ 2-CH₃—C₆H₄—CH₂ CH₃ CH₃CH₂ 3-CH₃—C₆H₄—CH₂CH₃ CH₃CH₂ 4-CH₃—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-CF₃—C₆H₄—CH₂ CH₃ CH₃CH₂4-CH₃CH₂—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-(CH₃)₂CH—C₆H₄—CH₂ CH₃ CH₃CH₂4-CH₃CH₂CH₂—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-(CH₃)₃C—C₆H₄—CH₂ CH₃ CH₃CH₂2,4-(CH₃)₂—C₆H₃—CH₂ CH₃ CH₃CH₂ 2,4,6-(CH₃)₃—C₆H₂—CH₂ CH₃ CH₃CH₂2,4-Cl₂—C₆H₃—CH₂ CH₃ CH₃CH₂ 3,4-Cl₂—C₆H₃—CH₂ CH₃ CH₃CH₂ 2,5-Cl₂—C₆H₃—CH₂CH₃ CH₃CH₂ 3,5-Cl₂—C₆H₃—CH₂ CH₃ CH₃CH₂ 2,6-Cl₂—C₆H₃—CH₂ CH₃ CH₃CH₂4-CH₃O—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-CF₃O—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-CH₃CH₂O—C₆H₄—CH₂CH₃ CH₃CH₂ 4-(CH₃)₂CHO—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-(CH₃)₃CO—C₆H₄—CH₂ CH₃CH₃CH₂ 4-CH₃OC(═O)—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CH₃CH₃CH₂ 4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CH₃ CH₃CH₂ 4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂CH₃ CH₃CH₂ 4-(CH₃)₃COC(═O)—C₆H₄—CH₂ CH₃ CH₃CH₂ CH₂Cl—CH₂ CH₃ CH₃CH₂CCl≡CCH₂ CH₃ CH₃CH₂ CBr≡CCH₂ CH₃ (CH₃)₂CH CH₃ CH₃ (CH₃)₂CH CH₃CH₂ CH₃(CH₃)₂CH CH₃CH₂CH₂ CH₃ (CH₃)₂CH (CH₃)₂CH CH₃ (CH₃)₂CH CH₃CH₂CH₂CH₂ CH₃(CH₃)₂CH CH₃CH₂—(CH₃)CH CH₃ (CH₃)₂CH (CH₃)₂CHCH₂ CH₃ (CH₃)₂CH (CH₃)₃CCH₃ (CH₃)₂CH CH₃CH₂CH₂CH₂CH₂ CH₃ (CH₃)₂CH (CH₃)₂CHCH₂CH₂ CH₃ (CH₃)₂CH(CH₃)₃CCH₂ CH₃ (CH₃)₂CH CH₃CH₂CH₂—(CH₃)CH CH₃ (CH₃)₂CH (CH₃)₂CH—(CH₃)CHCH₃ (CH₃)₂CH CH₃CH₂CH₂CH₂CH₂CH₂ CH₃ (CH₃)₂CH CH₂F CH₃ (CH₃)₂CH CH₂F—CH₂CH₃ (CH₃)₂CH CF₃CH₂ CH₃ (CH₃)₂CH CF₃CH₂CH₂ CH₃ (CH₃)₂CH CF₃CH₂CH₂CH₂ CH₃(CH₃)₂CH CF₃CH₂CH₂CH₂CH₂ CH₃ (CH₃)₂CH CH₂Cl—CH₂CH₂ CH₃ (CH₃)₂CHCH₂Br—CH₂CH₂ CH₃ (CH₃)₂CH CH₂Cl—CH₂CH₂CH₂ CH₃ (CH₃)₂CH CH₂Br—CH₂CH₂CH₂CH₃ (CH₃)₂CH CH₂Cl—CH₂CH₂CH₂CH₂ CH₃ (CH₃)₂CH CH₂Br—CH₂CH₂CH₂CH₂ CH₃(CH₃)₂CH CH₂═CHCH₂ CH₃ (CH₃)₂CH CH₂═C(CH₃)—CH₂ CH₃ (CH₃)₂CH(CH₃)₂C═CHCH₂ CH₃ (CH₃)₂CH CH₃CH═CHCH₂ CH₃ (CH₃)₂CH CH₂═CHCH₂CH₂ CH₃(CH₃)₂CH CH₃CH₂CH═CHCH₂ CH₃ (CH₃)₂CH CH₃CH═CHCH₂CH₂ CH₃ (CH₃)₂CHCH₃CH₂CH₂CH═CHCH₂ CH₃ (CH₃)₂CH CH₃CH₂CH═CHCH₂CH₂ CH₃ (CH₃)₂CH CHCl═CHCH₂CH₃ (CH₃)₂CH CCl₂═CHCH₂ CH₃ (CH₃)₂CH CHBr═CHCH₂ CH₃ (CH₃)₂CH CBr₂═CHCH₂CH₃ (CH₃)₂CH CH₂═CClCH₂ CH₃ (CH₃)₂CH CH₂═CBrCH₂ CH₃ (CH₃)₂CH CH₂═CFCH₂CH₃ (CH₃)₂CH CHCl═CClCH₂ CH₃ (CH₃)₂CH CHBr═CBrCH₂ CH₃ (CH₃)₂CHCH₃CCl═CHCH₂ CH₃ (CH₃)₂CH CF₃CCl═CHCH₂ CH₃ (CH₃)₂CH CClH₂CH═CHCH₂ CH₃(CH₃)₂CH CBrH₂CH═CHCH₂ CH₃ (CH₃)₂CH CF₂═CFCH₂ CH₃ (CH₃)₂CH CH≡CCH₂ CH₃(CH₃)₂CH CH₃C≡CCH₂ CH₃ (CH₃)₂CH CH₃CH₂C≡CCH₂ CH₃ (CH₃)₂CH CH₃C≡CCH₂CH₂CH₃ (CH₃)₂CH CH≡C—(CH₃)CH CH₃ (CH₃)₂CH N≡CCH₂ CH₃ (CH₃)₂CH N≡CCH₂CH₂ CH₃(CH₃)₂CH N≡CCH₂CH₂CH₂ CH₃ (CH₃)₂CH N≡CCH₂CH₂CH₂CH₂ CH₃ (CH₃)₂CH H CH₃(CH₃)₂CH C₆H₅—CH₂ CH₃ (CH₃)₂CH 2-F—C₆H₄—CH₂ CH₃ (CH₃)₂CH 3-F—C₆H₄—CH₂CH₃ (CH₃)₂CH 4-F—C₆H₄—CH₂ CH₃ (CH₃)₂CH 2-Cl—C₆H₄—CH₂ CH₃ (CH₃)₂CH3-Cl—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-Cl—C₆H₄—CH₂ CH₃ (CH₃)₂CH 2-Br—C₆H₄—CH₂ CH₃(CH₃)₂CH 3-Br—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-Br—C₆H₄—CH₂ CH₃ (CH₃)₂CH4-I—C₆H₄—CH₂ CH₃ (CH₃)₂CH 2-CH₃—C₆H₄—CH₂ CH₃ (CH₃)₂CH 3-CH₃—C₆H₄—CH₂ CH₃(CH₃)₂CH 4-CH₃—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-CF₃—C₆H₄—CH₂ CH₃ (CH₃)₂CH4-CH₃CH₂—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-(CH₃)₂CH—C₆H₄—CH₂ CH₃ (CH₃)₂CH4-CH₃CH₂CH₂—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-(CH₃)₃C—C₆H₄—CH₂ CH₃ (CH₃)₂CH2,4-(CH₃)₂—C₆H₃—CH₂ CH₃ (CH₃)₂CH 2,4,6-(CH₃)₃—C₆H₂—CH₂ CH₃ (CH₃)₂CH2,4-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₂CH 3,4-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₂CH2,5-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₂CH 3,5-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₂CH2,6-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₂CH 4-CH₃O—C₆H₄—CH₂ CH₃ (CH₃)₂CH4-CF₃O—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-CH₃CH₂O—C₆H₄—CH₂ CH₃ (CH₃)₂CH4-(CH₃)₂CHO—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-(CH₃)₃CO—C₆H₄—CH₂ CH₃ (CH₃)₂CH4-CH₃OC(═O)—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CH₃ (CH₃)₂CH4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CH₃ (CH₃)₂CH 4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CH₃(CH₃)₂CH 4-(CH₃)₃COC(═O)—C₆H₄—CH₂ CH₃ (CH₃)₂CH CH₂Cl—CH₂ CH₃ (CH₃)₂CHCCl≡CCH₂ CH₃ (CH₃)₂CH CBr≡CCH₂ CH₃ (CH₃)₃C CH₃ CH₃ (CH₃)₃C CH₃CH₂ CH₃(CH₃)₃C CH₃CH₂CH₂ CH₃ (CH₃)₃C (CH₃)₂CH CH₃ (CH₃)₃C CH₃CH₂CH₂CH₂ CH₃(CH₃)₃C CH₃CH₂—(CH₃)CH CH₃ (CH₃)₃C (CH₃)₂CHCH₂ CH₃ (CH₃)₃C (CH₃)₃C CH₃(CH₃)₃C CH₃CH₂CH₂CH₂CH₂ CH₃ (CH₃)₃C (CH₃)₂CHCH₂CH₂ CH₃ (CH₃)₃C(CH₃)₃CCH₂ CH₃ (CH₃)₃C CH₃CH₂CH₂—(CH₃)CH CH₃ (CH₃)₃C (CH₃)₂CH—(CH₃)CHCH₃ (CH₃)₃C CH₃CH₂CH₂CH₂CH₂CH₂ CH₃ (CH₃)₃C CH₂F CH₃ (CH₃)₃C CH₂F—CH₂ CH₃(CH₃)₃C CF₃CH₂ CH₃ (CH₃)₃C CF₃CH₂CH₂ CH₃ (CH₃)₃C CF₃CH₂CH₂CH₂ CH₃(CH₃)₃C CF₃CH₂CH₂CH₂CH₂ CH₃ (CH₃)₃C CH₂ClCH₂CH₂ CH₃ (CH₃)₃C CH₂Br—CH₂CH₂CH₃ (CH₃)₃C CH₂Cl—CH₂CH₂CH₂ CH₃ (CH₃)₃C CH₂Br—CH₂CH₂CH₂ CH₃ (CH₃)₃CCH₂Cl—CH₂CH₂CH₂CH₂ CH₃ (CH₃)₃C CH₂Br—CH₂CH₂CH₂CH₂ CH₃ (CH₃)₃C CH₂═CHCH₂CH₃ (CH₃)₃C CH₂═C(CH₃)—CH₂ CH₃ (CH₃)₃C (CH₃)₂C═CHCH₂ CH₃ (CH₃)₃CCH₃CH═CHCH₂ CH₃ (CH₃)₃C CH₂═CHCH₂CH₂ CH₃ (CH₃)₃C CH₃CH₂CH═CHCH₂ CH₃(CH₃)₃C CH₃CH═CHCH₂CH₂ CH₃ (CH₃)₃C CH₃CH₂CH₂CH═CHCH₂ CH₃ (CH₃)₃CCH₃CH₂CH═CHCH₂CH₂ CH₃ (CH₃)₃C CHCl═CHCH₂ CH₃ (CH₃)₃C CCl₂═CHCH₂ CH₃(CH₃)₃C CHBr═CHCH₂ CH₃ (CH₃)₃C CBr₂═CHCH₂ CH₃ (CH₃)₃C CH₂═CClCH₂ CH₃(CH₃)₃C CH₂═CBrCH₂ CH₃ (CH₃)₃C CH₂═CFCH₂ CH₃ (CH₃)₃C CHCl═CClCH₂ CH₃(CH₃)₃C CHBr═CBrCH₂ CH₃ (CH₃)₃C CH₃CCl═CHCH₂ CH₃ (CH₃)₃C CF₃CCl═CHCH₂CH₃ (CH₃)₃C CClH₂CH═CHCH₂ CH₃ (CH₃)₃C CBrH₂CH═CHCH₂ CH₃ (CH₃)₃CCF₂═CFCH₂ CH₃ (CH₃)₃C CH≡CCH₂ CH₃ (CH₃)₃C CH₃C≡CCH₂ CH₃ (CH₃)₃CCH₃CH₂C≡CCH₂ CH₃ (CH₃)₃C CH₃C≡CCH₂CH₂ CH₃ (CH₃)₃C CH≡C—(CH₃)CH CH₃(CH₃)₃C N≡CCH₂ CH₃ (CH₃)₃C N≡CCH₂CH₂ CH₃ (CH₃)₃C N≡CCH₂CH₂CH₂ CH₃(CH₃)₃C N≡CCH₂CH₂CH₂CH₂ CH₃ (CH₃)₃C H CH₃ (CH₃)₃C C₆H₅—CH₂ CH₃ (CH₃)₃C2-F—C₆H₄—CH₂ CH₃ (CH₃)₃C 3-F—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-F—C₆H₄—CH₂ CH₃(CH₃)₃C 2-Cl—C₆H₄—CH₂ CH₃ (CH₃)₃C 3-Cl—C₆H₄—CH₂ CH₃ (CH₃)₃C4-Cl—C₆H₄—CH₂ CH₃ (CH₃)₃C 2-Br—C₆H₄—CH₂ CH₃ (CH₃)₃C 3-Br—C₆H₄—CH₂ CH₃(CH₃)₃C 4-Br—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-I—C₆H₄—CH₂ CH₃ (CH₃)₃C2-CH₃—C₆H₄—CH₂ CH₃ (CH₃)₃C 3-CH₃—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-CH₃—C₆H₄—CH₂ CH₃(CH₃)₃C 4-CF₃—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-CH₃CH₂—C₆H₄—CH₂ CH₃ (CH₃)₃C4-(CH₃)₂CH—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-CH₃CH₂CH₂—C₆H₄—CH₂ CH₃ (CH₃)₃C4-(CH₃)₃C—C₆H₄—CH₂ CH₃ (CH₃)₃C 2,4-(CH₃)₂—C₆H₃—CH₂ CH₃ (CH₃)₃C2,4,6-(CH₃)₃—C₆H₂—CH₂ CH₃ (CH₃)₃C 2,4-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₃C3,4-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₃C 2,5-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₃C3,5-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₃C 2,6-Cl₂—C₆H₃—CH₂ CH₃ (CH₃)₃C4-CH₃O—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-CF₃O—C₆H₄—CH₂ CH₃ (CH₃)₃C4-CH₃CH₂O—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-(CH₃)₂CHO—C₆H₄—CH₂ CH₃ (CH₃)₃C4-(CH₃)₃CO—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-CH₃OC(═O)—C₆H₄—CH₂ CH₃ (CH₃)₃C4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CH₃(CH₃)₃C 4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CH₃ (CH₃)₃C 4-(CH₃)₃COC(═O)—C₆H₄—CH₂CH₃ (CH₃)₃C CH₂Cl—CH₂ CH₃ (CH₃)₃C CCl≡CCH₂ CH₃ (CH₃)₃C CBr≡CCH₂ CH₃CH₂CH₃ CH₃ CH₃CH₂ CH₃ CH₃CH₂ CH₃CH₂ CH₃ CH₃CH₂CH₂ CH₃CH₂ CH₃ (CH₃)₂CHCH₃CH₂ CH₃ CH₃CH₂CH₂CH₂ CH₃CH₂ CH₃ CH₃CH₂—(CH₃)CH CH₃CH₂ CH₃ (CH₃)₂CHCH₂CH₃CH₂ CH₃ 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CBr≡CCH₂ CH₃CH₂ (CH₃)₂CH CH₃ CH₃CH₂(CH₃)₂CH CH₃CH₂ CH₃CH₂ (CH₃)₂CH CH₃CH₂CH₂ CH₃CH₂ (CH₃)₂CH (CH₃)₂CHCH₃CH₂ (CH₃)₂CH CH₃CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CH CH₃CH₂—(CH₃)CH CH₃CH₂(CH₃)₂CH (CH₃)₂CHCH₂ CH₃CH₂ (CH₃)₂CH (CH₃)₃C CH₃CH₂ (CH₃)₂CHCH₃CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CH (CH₃)₂CHCH₂CH₂ CH₃CH₂ (CH₃)₂CH(CH₃)₃CCH₂ CH₃CH₂ (CH₃)₂CH CH₃CH₂CH₂—(CH₃)CH CH₃CH₂ (CH₃)₂CH(CH₃)₂CH—(CH₃)CH CH₃CH₂ (CH₃)₂CH CH₃CH₂CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CH CH₂FCH₃CH₂ (CH₃)₂CH CH₂F—CH₂ CH₃CH₂ (CH₃)₂CH CF₃CH₂ CH₃CH₂ (CH₃)₂CHCF₃CH₂CH₂ CH₃CH₂ (CH₃)₂CH CF₃CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CH CF₃CH₂CH₂CH₂CH₂CH₃CH₂ (CH₃)₂CH CH₂Cl—CH₂CH₂ CH₃CH₂ (CH₃)₂CH CH₂Br—CH₂CH₂ CH₃CH₂(CH₃)₂CH CH₂Cl—CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CH CH₂Br—CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CHCH₂Cl—CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CH CH₂Br—CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CHCH₂═CHCH₂ CH₃CH₂ (CH₃)₂CH CH₂═C(CH₃)—CH₂ CH₃CH₂ (CH₃)₂CH (CH₃)₂C═CHCH₂CH₃CH₂ (CH₃)₂CH CH₃CH═CHCH₂ CH₃CH₂ (CH₃)₂CH CH₂═CHCH₂CH₂ CH₃CH₂ (CH₃)₂CHCH₃CH₂CH═CHCH₂ CH₃CH₂ (CH₃)₂CH CH₃CH═CHCH₂CH₂ CH₃CH₂ (CH₃)₂CHCH₃CH₂CH₂CH═CHCH₂ CH₃CH₂ (CH₃)₂CH CH₃CH₂CH═CHCH₂CH₂ CH₃CH₂ (CH₃)₂CHCHCl═CHCH₂ CH₃CH₂ (CH₃)₂CH CCl₂═CHCH₂ CH₃CH₂ (CH₃)₂CH CHBr═CHCH₂ CH₃CH₂(CH₃)₂CH CBr₂═CHCH₂ CH₃CH₂ (CH₃)₂CH CH₂═CClCH₂ CH₃CH₂ (CH₃)₂CHCH₂═CBrCH₂ CH₃CH₂ (CH₃)₂CH CH₂═CFCH₂ CH₃CH₂ (CH₃)₂CH CHCl═CClCH₂ CH₃CH₂(CH₃)₂CH CHBr═CBrCH₂ CH₃CH₂ (CH₃)₂CH CH₃CCl═CHCH₂ CH₃CH₂ (CH₃)₂CHCF₃CCl═CHCH₂ CH₃CH₂ (CH₃)₂CH CClH₂CH═CHCH₂ CH₃CH₂ (CH₃)₂CH CBrH₂CH═CHCH₂CH₃CH₂ (CH₃)₂CH CF₂═CFCH₂ CH₃CH₂ (CH₃)₂CH CH≡CCH₂ CH₃CH₂ (CH₃)₂CHCH₃C≡CCH₂ CH₃CH₂ (CH₃)₂CH CH₃CH₂C≡CCH₂ CH₃CH₂ (CH₃)₂CH CH₃C≡CCH₂CH₂CH₃CH₂ (CH₃)₂CH CH≡C—(CH₃)CH CH₃CH₂ (CH₃)₂CH N≡CCH₂ CH₃CH₂ (CH₃)₂CHN≡CCH₂CH₂ CH₃CH₂ (CH₃)₂CH N≡CCH₂CH₂CH₂ CH₃CH₂ (CH₃)₂CH N≡CCH₂CH₂CH₂CH₂CH₃CH₂ (CH₃)₂CH H CH₃CH₂ (CH₃)₂CH C₆H₅—CH₂ CH₃CH₂ (CH₃)₂CH 2-F—C₆H₄—CH₂CH₃CH₂ (CH₃)₂CH 3-F—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-F—C₆H₄—CH₂ CH₃CH₂(CH₃)₂CH 2-Cl—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 3-Cl—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH4-Cl—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 2-Br—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH3-Br—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-Br—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-I—C₆H₄—CH₂CH₃CH₂ (CH₃)₂CH 2-CH₃—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 3-CH₃—C₆H₄—CH₂ CH₃CH₂(CH₃)₂CH 4-CH₃—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-CF₃—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH4-CH₃CH₂—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-(CH₃)₂CH—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH4-CH₃CH₂CH₂—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-(CH₃)₃C—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH2,4-(CH₃)₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₂CH 2,4,6-(CH₃)₃—C₆H₂—CH₂ CH₃CH₂(CH₃)₂CH 2,4-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₂CH 3,4-Cl₂—C₆H₃—CH₂ CH₃CH₂(CH₃)₂CH 2,5-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₂CH 3,5-Cl₂—C₆H₃—CH₂ CH₃CH₂(CH₃)₂CH 2,6-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₂CH 4-CH₃O—C₆H₄—CH₂ CH₃CH₂(CH₃)₂CH 4-CF₃O—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-CH₃CH₂O—C₆H₄—CH₂ CH₃CH₂(CH₃)₂CH 4-(CH₃)₂CHO—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-(CH₃)₃CO—C₆H₄—CH₂ CH₃CH₂(CH₃)₂CH 4-CH₃OC(═O)—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-CH₃CH₂OC(═O)—C₆H₄—CH₂CH₃CH₂ (CH₃)₂CH 4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CH₃CH₂ (CH₃)₂CH 4-(CH₃)₃COC(═O)—C₆H₄—CH₂CH₃CH₂ (CH₃)₂CH CH₂Cl—CH₂ CH₃CH₂ (CH₃)₂CH CCl≡CCH₂ CH₃CH₂ (CH₃)₂CHCBr≡CCH₂ CH₃CH₂ (CH₃)₃C CH₃ CH₃CH₂ (CH₃)₃C CH₃CH₂ CH₃CH₂ (CH₃)₃CCH₃CH₂CH₂ CH₃CH₂ (CH₃)₃C (CH₃)₂CH CH₃CH₂ (CH₃)₃C CH₃CH₂CH₂CH₂ CH₃CH₂(CH₃)₃C CH₃CH₂—(CH₃)CH CH₃CH₂ (CH₃)₃C (CH₃)₂CHCH₂ CH₃CH₂ (CH₃)₃C (CH₃)₃CCH₃CH₂ (CH₃)₃C CH₃CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃C (CH₃)₂CHCH₂CH₂ CH₃CH₂(CH₃)₃C (CH₃)₃CCH₂ CH₃CH₂ (CH₃)₃C CH₃CH₂CH₂—(CH₃)CH CH₃CH₂ (CH₃)₃C(CH₃)₂CH—(CH₃)CH CH₃CH₂ (CH₃)₃C CH₃CH₂CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃C CH₂FCH₃CH₂ (CH₃)₃C CH₂F—CH₂ CH₃CH₂ (CH₃)₃C CF₃CH₂ CH₃CH₂ (CH₃)₃C CF₃CH₂CH₂CH₃CH₂ (CH₃)₃C CF₃CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃C CF₃CH₂CH₂CH₂CH₂ CH₃CH₂(CH₃)₃C CH₂Cl—CH₂CH₂ CH₃CH₂ (CH₃)₃C CH₂Br—CH₂CH₂ CH₃CH₂ (CH₃)₃CCH₂Cl—CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃C CH₂Br—CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃CCH₂Cl—CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃C CH₂Br—CH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃CCH₂═CHCH₂ CH₃CH₂ (CH₃)₃C CH₂═C(CH₃)—CH₂ CH₃CH₂ (CH₃)₃C (CH₃)₂C═CHCH₂CH₃CH₂ (CH₃)₃C CH₃CH═CHCH₂ CH₃CH₂ (CH₃)₃C CH₂═CHCH₂CH₂ CH₃CH₂ (CH₃)₃CCH₃CH₂CH═CHCH₂ CH₃CH₂ (CH₃)₃C CH₃CH═CHCH₂CH₂ CH₃CH₂ (CH₃)₃CCH₃CH₂CH₂CH═CHCH₂ CH₃CH₂ (CH₃)₃C CH₃CH₂CH═CHCH₂CH₂ CH₃CH₂ (CH₃)₃CCHCl═CHCH₂ CH₃CH₂ (CH₃)₃C CCl₂═CHCH₂ CH₃CH₂ (CH₃)₃C CHBr═CHCH₂ CH₃CH₂(CH₃)₃C CBr₂═CHCH₂ CH₃CH₂ (CH₃)₃C CH₂═CClCH₂ CH₃CH₂ (CH₃)₃C CH₂═CBrCH₂CH₃CH₂ (CH₃)₃C CH₂═CFCH₂ CH₃CH₂ (CH₃)₃C CHCl═CClCH₂ CH₃CH₂ (CH₃)₃CCHBr═CBrCH₂ CH₃CH₂ (CH₃)₃C CH₃CCl═CHCH₂ CH₃CH₂ (CH₃)₃C CF₃CCl═CHCH₂CH₃CH₂ (CH₃)₃C CClH₂CH═CHCH₂ CH₃CH₂ (CH₃)₃C CBrH₂CH═CHCH₂ CH₃CH₂ (CH₃)₃CCF₂═CFCH₂ CH₃CH₂ (CH₃)₃C CH≡CCH₂ CH₃CH₂ (CH₃)₃C CH₃C≡CCH₂ CH₃CH₂ (CH₃)₃CCH₃CH₂C≡CCH₂ CH₃CH₂ (CH₃)₃C CH₃C≡CCH₂CH₂ CH₃CH₂ (CH₃)₃C CH≡C—(CH₃)CHCH₃CH₂ (CH₃)₃C N≡CCH₂ CH₃CH₂ (CH₃)₃C N≡CCH₂CH₂ CH₃CH₂ (CH₃)₃CN≡CCH₂CH₂CH₂ CH₃CH₂ (CH₃)₃C N≡CCH₂CH₂CH₂CH₂ CH₃CH₂ (CH₃)₃C H CH₃CH₂(CH₃)₃C C₆H₅—CH₂ CH₃CH₂ (CH₃)₃C 2-F—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 3-F—C₆H₄—CH₂CH₃CH₂ (CH₃)₃C 4-F—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 2-Cl—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C3-Cl—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-Cl—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 2-Br—C₆H₄—CH₂CH₃CH₂ (CH₃)₃C 3-Br—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-Br—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C4-I—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 2-CH₃—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 3-CH₃—C₆H₄—CH₂CH₃CH₂ (CH₃)₃C 4-CH₃—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-CF₃—C₆H₄—CH₂ CH₃CH₂(CH₃)₃C 4-CH₃CH₂—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-(CH₃)₂CH—C₆H₄—CH₂ CH₃CH₂(CH₃)₃C 4-CH₃CH₂CH₂—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-(CH₃)₃C—C₆H₄—CH₂ CH₃CH₂(CH₃)₃C 2,4-(CH₃)₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₃C 2,4,6-(CH₃)₃—C₆H₂—CH₂ CH₃CH₂(CH₃)₃C 2,4-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₃C 3,4-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₃C2,5-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₃C 3,5-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₃C2,6-Cl₂—C₆H₃—CH₂ CH₃CH₂ (CH₃)₃C 4-CH₃O—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C4-CF₃O—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-CH₃CH₂O—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C4-(CH₃)₂CHO—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-(CH₃)₃CO—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C4-CH₃OC(═O)—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CH₃CH₂(CH₃)₃C 4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CH₃CH₂ (CH₃)₃C 4-(CH₃)₃COC(═O)—C₆H₄—CH₂ CH₃CH₂(CH₃)₃C CH₂Cl—CH₂ CH₃CH₂ (CH₃)₃C CCl≡CCH₂ CH₃CH₂ (CH₃)₃C CBr≡CCH₂ CF₃CH₃ CH₃ CF₃ CH₃ CH₃CH₂ CF₃ CH₃ CH₃CH₂CH₂ CF₃ CH₃ (CH₃)₂CH CF₃ CH₃CH₃CH₂CH₂CH₂ CF₃ CH₃ CH₃CH₂—(CH₃)CH CF₃ CH₃ (CH₃)₂CHCH₂ CF₃ CH₃ (CH₃)₃CCF₃ CH₃ CH₃CH₂CH₂CH₂CH₂ CF₃ CH₃ (CH₃)₂CHCH₂CH₂ CF₃ CH₃ (CH₃)₃CCH₂ CF₃CH₃ CH₃CH₂CH₂—(CH₃)CH CF₃ CH₃ (CH₃)₂CH—(CH₃)CH CF₃ CH₃CH₃CH₂CH₂CH₂CH₂CH₂ CF₃ CH₃ CH₂F CF₃ CH₃ CH₂FCH₂ CF₃ CH₃ CF₃CH₂ CF₃ CH₃CF₃CH₂CH₂ CF₃ CH₃ CF₃CH₂CH₂CH₂ CF₃ CH₃ CF₃CH₂CH₂CH₂CH₂ CF₃ CH₃CH₂ClCH₂CH₂ CF₃ CH₃ CH₂BrCH₂CH₂ CF₃ CH₃ CH₂ClCH₂CH₂CH₂ CF₃ CH₃CH₂BrCH₂CH₂CH₂ CF₃ CH₃ CH₂ClCH₂CH₂CH₂CH₂ CF₃ CH₃ CH₂BrCH₂CH₂CH₂CH₂ CF₃CH₃ CH₂═CHCH₂ CF₃ CH₃ CH₂═C(CH₃)—CH₂ CF₃ CH₃ (CH₃)₂C═CHCH₂ CF₃ CH₃CH₃CH═CHCH₂ CF₃ CH₃ CH₂═CHCH₂CH₂ CF₃ CH₃ CH₃CH₂CH═CHCH₂ CF₃ CH₃CH₃CH═CHCH₂CH₂ CF₃ CH₃ CH₃CH₂CH₂CH═CHCH₂ CF₃ CH₃ CH₃CH₂CH═CHCH₂CH₂ CF₃CH₃ CHCl═CHCH₂ CF₃ CH₃ CCl₂═CHCH₂ CF₃ CH₃ CHBr═CHCH₂ CF₃ CH₃ CBr₂═CHCH₂CF₃ CH₃ CH₂═CClCH₂ CF₃ CH₃ CH₂═CBrCH₂ CF₃ CH₃ CH₂═CFCH₂ CF₃ CH₃CHCl═CClCH₂ CF₃ CH₃ CHBr═CBrCH₂ CF₃ CH₃ CH₃CCl═CHCH₂ CF₃ CH₃CF₃CCl═CHCH₂ CF₃ CH₃ CClH₂—CH═CHCH₂ CF₃ CH₃ CBrH₂—CH═CHCH₂ CF₃ CH₃CF₂═CFCH₂ CF₃ CH₃ CH≡CCH₂ CF₃ CH₃ CH₃C≡CCH₂ CF₃ CH₃ CH₃CH₂C≡CCH₂ CF₃ CH₃CH₃C≡CCH₂CH₂ CF₃ CH₃ CH≡C—(CH₃)CH CF₃ CH₃ N≡CCH₂ CF₃ CH₃ N≡CCH₂CH₂ CF₃CH₃ N≡CCH₂CH₂CH₂ CF₃ CH₃ N≡CCH₂CH₂CH₂CH₂ CF₃ CH₃ H CF₃ CH₃ C₆H₅—CH₂ CF₃CH₃ 2-F—C₆H₄—CH₂ CF₃ CH₃ 3-F—C₆H₄—CH₂ CF₃ CH₃ 4-F—C₆H₄—CH₂ CF₃ CH₃2-Cl—C₆H₄—CH₂ CF₃ CH₃ 3-Cl—C₆H₄—CH₂ CF₃ CH₃ 4-Cl—C₆H₄—CH₂ CF₃ CH₃2-Br—C₆H₄—CH₂ CF₃ CH₃ 3-Br—C₆H₄—CH₂ CF₃ CH₃ 4-Br—C₆H₄—CH₂ CF₃ CH₃4-I—C₆H₄—CH₂ CF₃ CH₃ 2-CH₃—C₆H₄—CH₂ CF₃ CH₃ 3-CH₃—C₆H₄—CH₂ CF₃ CH₃4-CH₃—C₆H₄—CH₂ CF₃ CH₃ 4-CF₃—C₆H₄—CH₂ CF₃ CH₃ 4-CH₃CH₂—C₆H₄—CH₂ CF₃ CH₃4-(CH₃)₂CH—C₆H₄—CH₂ CF₃ CH₃ 4-CH₃CH₂CH₂—C₆H₄—CH₂ CF₃ CH₃4-(CH₃)₃C—C₆H₄—CH₂ CF₃ CH₃ 2,4-(CH₃)₂—C₆H₃—CH₂ CF₃ CH₃2,4,6-(CH₃)₃—C₆H₂—CH₂ CF₃ CH₃ 2,4-Cl₂—C₆H₃—CH₂ CF₃ CH₃ 3,4-Cl₂—C₆H₃—CH₂CF₃ CH₃ 2,5-Cl₂—C₆H₃—CH₂ CF₃ CH₃ 3,5-Cl₂—C₆H₃—CH₂ CF₃ CH₃2,6-Cl₂—C₆H₃—CH₂ CF₃ CH₃ 4-CH₃O—C₆H₄—CH₂ CF₃ CH₃ 4-CF₃O—C₆H₄—CH₂ CF₃ CH₃4-CH₃CH₂O—C₆H₄—CH₂ CF₃ CH₃ 4-(CH₃)₂CHO—C₆H₄—CH₂ CF₃ CH₃4-(CH₃)₃CO—C₆H₄—CH₂ CF₃ CH₃ 4-CH₃OC(═O)—C₆H₄—CH₂ CF₃ CH₃4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CF₃ CH₃ 4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CF₃ CH₃4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CF₃ CH₃ 4-(CH₃)₃COC(═O)—C₆H₄—CH₂ CF₃ CH₃CH₂Cl—CH₂ CF₃ CH₃ CCl≡CCH₂ CF₃ CH₃ CBr≡CCH₂ CF₃ CH₃CH₂ CH₃ CF₃ CH₃CH₂CH₃CH₂ CF₃ CH₃CH₂ CH₃CH₂CH₂ CF₃ CH₃CH₂ (CH₃)₂CH CF₃ CH₃CH₂ CH₃CH₂CH₂CH₂CF₃ CH₃CH₂ CH₃CH₂—(CH₃)CH CF₃ CH₃CH₂ (CH₃)₂CHCH₂ CF₃ CH₃CH₂ (CH₃)₃C CF₃CH₃CH₂ CH₃CH₂CH₂CH₂CH₂ CF₃ CH₃CH₂ (CH₃)₂CHCH₂CH₂ CF₃ CH₃CH₂ (CH₃)₃CCH₂CF₃ CH₃CH₂ CH₃CH₂CH₂—(CH₃)CH CF₃ CH₃CH₂ (CH₃)₂CH—(CH₃)CH CF₃ CH₃CH₂CH₃CH₂CH₂CH₂CH₂CH₂ CF₃ CH₃CH₂ CH₂F CF₃ CH₃CH₂ CH₂F—CH₂ CF₃ CH₃CH₂ CF₃CH₂CF₃ CH₃CH₂ CF₃CH₂CH₂ CF₃ CH₃CH₂ CF₃CH₂CH₂CH₂ CF₃ CH₃CH₂ CF₃CH₂CH₂CH₂CH₂CF₃ CH₃CH₂ CH₂Cl—CH₂CH₂ CF₃ CH₃CH₂ CH₂Br—CH₂CH₂ CF₃ CH₃CH₂CH₂Cl—CH₂CH₂CH₂ CF₃ CH₃CH₂ CH₂Br—CH₂CH₂CH₂ CF₃ CH₃CH₂ CH₂Cl—CH₂CH₂CH₂CH₂CF₃ CH₃CH₂ CH₂Br—CH₂CH₂CH₂CH₂ CF₃ CH₃CH₂ CH₂═CHCH₂ CF₃ CH₃CH₂CH₂═C(CH₃)—CH₂ CF₃ CH₃CH₂ (CH₃)₂C═CHCH₂ CF₃ CH₃CH₂ CH₃CH═CHCH₂ CF₃CH₃CH₂ CH₂═CHCH₂CH₂ CF₃ CH₃CH₂ CH₃CH₂CH═CHCH₂ CF₃ CH₃CH₂ CH₃CH═CHCH₂CH₂CF₃ CH₃CH₂ CH₃CH₂CH₂CH═CHCH₂ CF₃ CH₃CH₂ CH₃CH₂CH═CHCH₂CH₂ CF₃ CH₃CH₂CHCl═CHCH₂ CF₃ CH₃CH₂ CCl₂═CHCH₂ CF₃ CH₃CH₂ CHBr═CHCH₂ CF₃ CH₃CH₂CBr₂═CHCH₂ CF₃ CH₃CH₂ CH₂═CClCH₂ CF₃ CH₃CH₂ CH₂═CBrCH₂ CF₃ CH₃CH₂CH₂═CFCH₂ CF₃ CH₃CH₂ CHCl═CClCH₂ CF₃ CH₃CH₂ CHBr═CBrCH₂ CF₃ CH₃CH₂CH₃CCl═CHCH₂ CF₃ CH₃CH₂ CF₃CCl═CHCH₂ CF₃ CH₃CH₂ CClH₂—CH═CHCH₂ CF₃CH₃CH₂ CBrH₂—CH═CHCH₂ CF₃ CH₃CH₂ CF₂═CFCH₂ CF₃ CH₃CH₂ CH≡CCH₂ CF₃ CH₃CH₂CH₃C≡CCH₂ CF₃ CH₃CH₂ CH₃CH₂C≡CCH₂ CF₃ CH₃CH₂ CH₃C≡CCH₂CH₂ CF₃ CH₃CH₂CH≡C—(CH₃)CH CF₃ CH₃CH₂ N≡CCH₂ CF₃ CH₃CH₂ N≡CCH₂CH₂ CF₃ CH₃CH₂N≡CCH₂CH₂CH₂ CF₃ CH₃CH₂ N≡CCH₂CH₂CH₂CH₂ CF₃ CH₃CH₂ H CF₃ CH₃CH₂ C₆H₅—CH₂CF₃ CH₃CH₂ 2-F—C₆H₄—CH₂ CF₃ CH₃CH₂ 3-F—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-F—C₆H₄—CH₂CF₃ CH₃CH₂ 2-Cl—C₆H₄—CH₂ CF₃ CH₃CH₂ 3-Cl—C₆H₄—CH₂ CF₃ CH₃CH₂4-Cl—C₆H₄—CH₂ CF₃ CH₃CH₂ 2-Br—C₆H₄—CH₂ CF₃ CH₃CH₂ 3-Br—C₆H₄—CH₂ CF₃CH₃CH₂ 4-Br—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-I—C₆H₄—CH₂ CF₃ CH₃CH₂ 2-CH₃—C₆H₄—CH₂CF₃ CH₃CH₂ 3-CH₃—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-CH₃—C₆H₄—CH₂ CF₃ CH₃CH₂4-CF₃—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-CH₃CH₂—C₆H₄—CH₂ CF₃ CH₃CH₂4-(CH₃)₂CH—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-CH₃CH₂CH₂—C₆H₄—CH₂ CF₃ CH₃CH₂4-(CH₃)₃C—C₆H₄—CH₂ CF₃ CH₃CH₂ 2,4-(CH₃)₂—C₆H₃—CH₂ CF₃ CH₃CH₂2,4,6-(CH₃)₃—C₆H₂—CH₂ CF₃ CH₃CH₂ 2,4-Cl₂—C₆H₃—CH₂ CF₃ CH₃CH₂3,4-Cl₂—C₆H₃—CH₂ CF₃ CH₃CH₂ 2,5-Cl₂—C₆H₃—CH₂ CF₃ CH₃CH₂ 3,5-Cl₂—C₆H₃—CH₂CF₃ CH₃CH₂ 2,6-Cl₂—C₆H₃—CH₂ CF₃ CH₃CH₂ 4-CH₃O—C₆H₄—CH₂ CF₃ CH₃CH₂4-CF₃O—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-CH₃CH₂O—C₆H₄—CH₂ CF₃ CH₃CH₂4-(CH₃)₂CHO—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-(CH₃)₃CO—C₆H₄—CH₂ CF₃ CH₃CH₂4-CH₃OC(═O)—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CF₃ CH₃CH₂4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CF₃ CH₃CH₂ 4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CF₃CH₃CH₂ 4-(CH₃)₃COC(═O)—C₆H₄—CH₂ CF₃ CH₃CH₂ CH₂Cl—CH₂ CF₃ CH₃CH₂ CCl≡CCH₂CF₃ CH₃CH₂ CBr≡CCH₂ CF₃ (CH₃)₂CH CH₃ CF₃ (CH₃)₂CH CH₃CH₂ CF₃ (CH₃)₂CHCH₃CH₂CH₂ CF₃ (CH₃)₂CH (CH₃)₂CH CF₃ (CH₃)₂CH CH₃CH₂CH₂CH₂ CF₃ (CH₃)₂CHCH₃CH₂—(CH₃)CH CF₃ (CH₃)₂CH (CH₃)₂CHCH₂ CF₃ (CH₃)₂CH (CH₃)₃C CF₃(CH₃)₂CH CH₃CH₂CH₂CH₂CH₂ CF₃ (CH₃)₂CH (CH₃)₂CHCH₂CH₂ CF₃ (CH₃)₂CH(CH₃)₃CCH₂ CF₃ (CH₃)₂CH CH₃CH₂CH₂—(CH₃)CH CF₃ (CH₃)₂CH (CH₃)₂CH—(CH₃)CHCF₃ (CH₃)₂CH CH₃CH₂CH₂CH₂CH₂CH₂ CF₃ (CH₃)₂CH CH₂F CF₃ (CH₃)₂CH CH₂F—CH₂CF₃ (CH₃)₂CH CF₃CH₂ CF₃ (CH₃)₂CH CF₃CH₂CH₂ CF₃ (CH₃)₂CH CF₃CH₂CH₂CH₂ CF₃(CH₃)₂CH CF₃CH₂CH₂CH₂CH₂ CF₃ (CH₃)₂CH CH₂Cl—CH₂CH₂ CF₃ (CH₃)₂CHCH₂Br—CH₂CH₂ CF₃ (CH₃)₂CH CH₂Cl—CH₂CH₂CH₂ CF₃ (CH₃)₂CH CH₂Br—CH₂CH₂CH₂CF₃ (CH₃)₂CH CH₂Cl—CH₂CH₂CH₂CH₂ CF₃ (CH₃)₂CH CH₂Br—CH₂CH₂CH₂CH₂ CF₃(CH₃)₂CH CH₂═CHCH₂ CF₃ (CH₃)₂CH CH₂═C(CH₃)CH₂ CF₃ (CH₃)₂CH (CH₃)₂C═CHCH₂CF₃ (CH₃)₂CH CH₃CH═CHCH₂ CF₃ (CH₃)₂CH CH₂═CHCH₂CH₂ CF₃ (CH₃)₂CHCH₃CH₂CH═CHCH₂ CF₃ (CH₃)₂CH CH₃CH═CHCH₂CH₂ CF₃ (CH₃)₂CHCH₃CH₂CH₂CH═CHCH₂ CF₃ (CH₃)₂CH CH₃CH₂CH═CHCH₂CH₂ CF₃ (CH₃)₂CH CHCl═CHCH₂CF₃ (CH₃)₂CH CCl₂═CHCH₂ CF₃ (CH₃)₂CH CHBr═CHCH₂ CF₃ (CH₃)₂CH CBr₂═CHCH₂CF₃ (CH₃)₂CH CH₂═CClCH₂ CF₃ (CH₃)₂CH CH₂═CBrCH₂ CF₃ (CH₃)₂CH CH₂═CFCH₂CF₃ (CH₃)₂CH CHCl═CClCH₂ CF₃ (CH₃)₂CH CHBr═CBrCH₂ CF₃ (CH₃)₂CHCH₃CCl═CHCH₂ CF₃ (CH₃)₂CH CF₃CCl═CHCH₂ CF₃ (CH₃)₂CH CClH₂—CH═CHCH₂ CF₃(CH₃)₂CH CBrH₂—CH═CHCH₂ CF₃ (CH₃)₂CH CF₂═CFCH₂ CF₃ (CH₃)₂CH CH≡CCH₂ CF₃(CH₃)₂CH CH₃C≡CCH₂ CF₃ (CH₃)₂CH CH₃CH₂C≡CCH₂ CF₃ (CH₃)₂CH CH₃C≡CCH₂CH₂CF₃ (CH₃)₂CH CH≡C—(CH₃)CH CF₃ (CH₃)₂CH N≡CCH₂ CF₃ (CH₃)₂CH N≡CCH₂CH₂ CF₃(CH₃)₂CH N≡CCH₂CH₂CH₂ CF₃ (CH₃)₂CH N≡CCH₂CH₂CH₂CH₂ CF₃ (CH₃)₂CH H CF₃(CH₃)₂CH C₆H₅—CH₂ CF₃ (CH₃)₂CH 2-F—C₆H₄—CH₂ CF₃ (CH₃)₂CH 3-F—C₆H₄—CH₂CF₃ (CH₃)₂CH 4-F—C₆H₄—CH₂ CF₃ (CH₃)₂CH 2-Cl—C₆H₄—CH₂ CF₃ (CH₃)₂CH3-Cl—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-Cl—C₆H₄—CH₂ CF₃ (CH₃)₂CH 2-Br—C₆H₄—CH₂ CF₃(CH₃)₂CH 3-Br—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-Br—C₆H₄—CH₂ CF₃ (CH₃)₂CH4-I—C₆H₄—CH₂ CF₃ (CH₃)₂CH 2-CH₃—C₆H₄—CH₂ CF₃ (CH₃)₂CH 3-CH₃—C₆H₄—CH₂ CF₃(CH₃)₂CH 4-CH₃—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-CF₃—C₆H₄—CH₂ CF₃ (CH₃)₂CH4-CH₃CH₂—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-(CH₃)₂CH—C₆H₄—CH₂ CF₃ (CH₃)₂CH4-CH₃CH₂CH₂—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-(CH₃)₃C—C₆H₄—CH₂ CF₃ (CH₃)₂CH2,4-(CH₃)₂—C₆H₃—CH₂ CF₃ (CH₃)₂CH 2,4,6-(CH₃)₃—C₆H₂—CH₂ CF₃ (CH₃)₂CH2,4-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₂CH 3,4-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₂CH2,5-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₂CH 3,5-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₂CH2,6-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₂CH 4-CH₃O—C₆H₄—CH₂ CF₃ (CH₃)₂CH4-CF₃O—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-CH₃CH₂O—C₆H₄—CH₂ CF₃ (CH₃)₂CH4-(CH₃)₂CHO—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-(CH₃)₃CO—C₆H₄—CH₂ CF₃ (CH₃)₂CH4-CH₃OC(═O)—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CF₃ (CH₃)₂CH4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CF₃ (CH₃)₂CH 4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CF₃(CH₃)₂CH 4-(CH₃)₃COC(═O)—C₆H₄—CH₂ CF₃ (CH₃)₂CH CH₂Cl—CH₂ CF₃ (CH₃)₂CHCCl≡CCH₂ CF₃ (CH₃)₂CH CBr≡CCH₂ CF₃ (CH₃)₃C CH₃ CF₃ (CH₃)₃C CH₃CH₂ CF₃(CH₃)₃C CH₃CH₂CH₂ CF₃ (CH₃)₃C (CH₃)₂CH CF₃ (CH₃)₃C CH₃CH₂CH₂CH₂ CF₃(CH₃)₃C CH₃CH₂—(CH₃)CH CF₃ (CH₃)₃C (CH₃)₂CHCH₂ CF₃ (CH₃)₃C (CH₃)₃C CF₃(CH₃)₃C CH₃CH₂CH₂CH₂CH₂ CF₃ (CH₃)₃C (CH₃)₂CHCH₂CH₂ CF₃ (CH₃)₃C(CH₃)₃CCH₂ CF₃ (CH₃)₃C CH₃CH₂CH₂—(CH₃)CH CF₃ (CH₃)₃C (CH₃)₂CH—(CH₃)CHCF₃ (CH₃)₃C CH₃CH₂CH₂CH₂CH₂CH₂ CF₃ (CH₃)₃C CH₂F CF₃ (CH₃)₃C CH₂F—CH₂ CF₃(CH₃)₃C CF₃CH₂ CF₃ (CH₃)₃C CF₃CH₂CH₂ CF₃ (CH₃)₃C CF₃CH₂CH₂CH₂ CF₃(CH₃)₃C CF₃CH₂CH₂CH₂CH₂ CF₃ (CH₃)₃C CH₂Cl—CH₂CH₂ CF₃ (CH₃)₃CCH₂Br—CH₂CH₂ CF₃ (CH₃)₃C CH₂Cl—CH₂CH₂CH₂ CF₃ (CH₃)₃C CH₂Br—CH₂CH₂CH₂ CF₃(CH₃)₃C CH₂Cl—CH₂CH₂CH₂CH₂ CF₃ (CH₃)₃C CH₂BrCH₂CH₂CH₂CH₂ CF₃ (CH₃)₃CCH₂═CHCH₂ CF₃ (CH₃)₃C CH₂═C(CH₃)—CH₂ CF₃ (CH₃)₃C (CH₃)₂C═CHCH₂ CF₃(CH₃)₃C CH₃CH═CHCH₂ CF₃ (CH₃)₃C CH₂═CHCH₂CH₂ CF₃ (CH₃)₃C CH₃CH₂CH═CHCH₂CF₃ (CH₃)₃C CH₃CH═CHCH₂CH₂ CF₃ (CH₃)₃C CH₃CH₂CH₂CH═CHCH₂ CF₃ (CH₃)₃CCH₃CH₂CH═CHCH₂CH₂ CF₃ (CH₃)₃C CHCl═CHCH₂ CF₃ (CH₃)₃C CCl₂═CHCH₂ CF₃(CH₃)₃C CHBr═CHCH₂ CF₃ (CH₃)₃C CBr₂═CHCH₂ CF₃ (CH₃)₃C CH₂═CClCH₂ CF₃(CH₃)₃C CH₂═CBrCH₂ CF₃ (CH₃)₃C CH₂═CFCH₂ CF₃ (CH₃)₃C CHCl═CClCH₂ CF₃(CH₃)₃C CHBr═CBrCH₂ CF₃ (CH₃)₃C CH₃CCl═CHCH₂ CF₃ (CH₃)₃C CF₃CCl═CHCH₂CF₃ (CH₃)₃C CClH₂CH═CHCH₂ CF₃ (CH₃)₃C CBrH₂CH═CHCH₂ CF₃ (CH₃)₃CCF₂═CFCH₂ CF₃ (CH₃)₃C CH≡CCH₂ CF₃ (CH₃)₃C CH₃C≡CCH₂ CF₃ (CH₃)₃CCH₃CH₂C≡CCH₂ CF₃ (CH₃)₃C CH₃C≡CCH₂CH₂ CF₃ (CH₃)₃C CH≡C—(CH₃)CH CF₃(CH₃)₃C N≡CCH₂ CF₃ (CH₃)₃C N≡CCH₂CH₂ CF₃ (CH₃)₃C N≡CCH₂CH₂CH₂ CF₃(CH₃)₃C N≡CCH₂CH₂CH₂CH₂ CF₃ (CH₃)₃C H CF₃ (CH₃)₃C C₆H₅—CH₂ CF₃ (CH₃)₃C2-F—C₆H₄—CH₂ CF₃ (CH₃)₃C 3-F—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-F—C₆H₄—CH₂ CF₃(CH₃)₃C 2-Cl—C₆H₄—CH₂ CF₃ (CH₃)₃C 3-Cl—C₆H₄—CH₂ CF₃ (CH₃)₃C4-Cl—C₆H₄—CH₂ CF₃ (CH₃)₃C 2-Br—C₆H₄—CH₂ CF₃ (CH₃)₃C 3-Br—C₆H₄—CH₂ CF₃(CH₃)₃C 4-Br—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-I—C₆H₄—CH₂ CF₃ (CH₃)₃C2-CH₃—C₆H₄—CH₂ CF₃ (CH₃)₃C 3-CH₃—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-CH₃—C₆H₄—CH₂ CF₃(CH₃)₃C 4-CF₃—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-CH₃CH₂—C₆H₄—CH₂ CF₃ (CH₃)₃C4-(CH₃)₂CH—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-CH₃CH₂CH₂—C₆H₄—CH₂ CF₃ (CH₃)₃C4-(CH₃)₃C—C₆H₄—CH₂ CF₃ (CH₃)₃C 2,4-(CH₃)₂—C₆H₃—CH₂ CF₃ (CH₃)₃C2,4,6-(CH₃)₃—C₆H₂—CH₂ CF₃ (CH₃)₃C 2,4-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₃C3,4-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₃C 2,5-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₃C3,5-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₃C 2,6-Cl₂—C₆H₃—CH₂ CF₃ (CH₃)₃C4-CH₃O—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-CF₃O—C₆H₄—CH₂ CF₃ (CH₃)₃C4-CH₃CH₂O—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-(CH₃)₂CHO—C₆H₄—CH₂ CF₃ (CH₃)₃C4-(CH₃)₃CO—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-CH₃OC(═O)—C₆H₄—CH₂ CF₃ (CH₃)₃C4-CH₃CH₂OC(═O)—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-CH₃CH₂CH₂OC(═O)—C₆H₄—CH₂ CF₃(CH₃)₃C 4-(CH₃)₂CHOC(═O)—C₆H₄—CH₂ CF₃ (CH₃)₃C 4-(CH₃)₃COC(═O)—C₆H₄—CH₂CF₃ (CH₃)₃C CH₂Cl—CH₂ CF₃ (CH₃)₃C CCl≡CCH₂ CF₃ (CH₃)₃C CBr≡CCH₂ (CH₃)₂CHCH₃ H (CH₃)₂CH CH₃ CH₃ (CH₃)₂CH CH₃ CH₃CH₂ (CH₃)₂CH CH₃ CH₃CH₂CH₂(CH₃)₂CH CH₃ CH₂F (CH₃)₂CH CH₃ CF₃CH₂ (CH₃)₂CH CH₃ CF₃CH₂CH₂ (CH₃)₂CHCH₃ CH₂ClCH₂ (CH₃)₂CH CH₃ CH₂═CHCH₂ (CH₃)₂CH CH₃ CH≡CCH₂ (CH₃)₂CH CH₃CH₃C≡CCH₂ (CH₃)₂CH CH₃ N≡CCH₂ (CH₃)₃C CH₃ H (CH₃)₃C CH₃ CH₃ (CH₃)₃C CH₃CH₃CH₂ (CH₃)₃C CH₃ CH₃CH₂CH₂ (CH₃)₃C CH₃ CH₂F (CH₃)₃C CH₃ CF₃CH₂ (CH₃)₃CCH₃ CF₃CH₂CH₂ (CH₃)₃C CH₃ CH₂Cl—CH₂ (CH₃)₃C CH₃ CH₂═CHCH₂ (CH₃)₃C CH₃CH≡CCH₂ (CH₃)₃C CH₃ CH₃C≡CCH₂ (CH₃)₃C CH₃ N≡CCH₂

TABLE 2 (X represents an oxygen atom) R¹ R² CH₃ CH₃ CH₃ CH₃CH₂ CH₃(CH₃)₂CH CH₃ (CH₃)₃C CH₃CH₂ CH₃ CH₃CH₂ CH₃CH₂ CH₃CH₂ (CH₃)₂CH CH₃CH₂(CH₃)₃C CH₃CH₂ CH₃ CH₃CH₂ CH₃CH₂ CH₃CH₂ (CH₃)₂CH CH₃CH₂ (CH₃)₃C (CH₃)₃CCH₃ (CH₃)₃C CH₃CH₂ (CH₃)₃C (CH₃)₂CH (CH₃)₃C (CH₃)₃C (CH₃)₂CH CH₃(CH₃)₂CH CH₃CH₂ (CH₃)₂CH (CH₃)₂CH (CH₃)₂CH (CH₃)₃C CF₃ CH₃ CF₃ CH₃CH₂CF₃ (CH₃)₂CH CF₃ (CH₃)₃CThe noxious arthropods against which the compound of the presentinvention has activity may include insect pests and acarine pests, andconcretely described below:Hemiptera:

Delphacidae such as Laodelphax striatellus, Nilaparvata lugens,Sogatella furcifera and the like,

Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescensand the like,

Aphididae such as Aphis gossypii, Myzus persicae and the like,

Pentatomidae such as Nezara antennata, Riptortus clavetus and the like,

Aleyrodidae such as Trialeurodes vaporariorum, Bemisia argentifolii andthe like,

Coccidae such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspiscitri, Ceroplastes rubens, Icerya purchasi and the like,

Tingidae,

Psyllidae, and the like;

Lepidoptera:

Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarchaderogata, Plodia interpunctella and the like,

Noctuidae such as Spodoptera litura, Pseudaletia separata, Thoricoplusiaspp., Heliothis spp., Helicoverpa spp. and the like,

Pieridae such as Pieris rapae and the like,

Tortricidae such as Adoxophyes spp., Grapholita molesta, Cydia pomonellaand the like,

Carposinidae such as Carposina niponensis and the like,

Lyonetiidae such as Lyonetia spp. and the like,

Lymantriidae such as Lymantria spp., Euproctis spp., and the like,

Yponomeutidae such as Plutella xylostella and the like,

Gelechiidae such as Pectinophora gossypiella and the like,

Arctiidae such as Hyphantria cunea and the like,

Tineidae such as Tinea translucens, Tineola bisselliella and the like;

Diptera:

Calicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culexquinquefasciatus and the like,

Aedes spp. such as Aedes aegypti, Aedes albopictus and the like,

Anopheles such as Anopheles sinensis and the like,

Chironomidae,

Muscidae such as Musca domestica, Muscina stabulans and the like,

Calliphoridae,

Sarcophagidae,

Fanniidae,

Anthomyiidae such as Delia platura, Delia antiqua and the like,

Tephritidae,

Drosophilidae,

Psychodidae,

Tabanidae,

Simuliidae,

Stomoxyidae,

Agromyzidae, and the like;

Coleoptera:

Diabrotica spp. such as Diabrotica virgifera virgifera, Diabroticaundecimpunctata howardi and the like,

Scarabaeidae such as Anomala cuprea, Anomala rufocuprea and the like,

Curculionidae such as Sitophilus zeamais, Lissorhoptrus oryzophilus,Callosobruchuys chienensis and the like,

Tenebrionidae such as Tenebrio molitor, Tribolium castaneum and thelike,

Chrysomelidae such as Aulacophora femoralis, Phyllotreta striolata,Leptinotarsa decemlineata and the like,

Anobiidae,

Epilachna spp. such as Epilachna vigintioctopunctata and the like,

Lyctidae,

Bostrychidae,

Cerambycidae,

Paederus fuscipes;

Blattodea:

Blattella germanica, Periplaneta fulginosa, Periplaneta americana,Periplaneta brunnea, Blatta orientalis and the like;

Thysanoptera:

Thrips palmi, Thrips tahaci, Frankliniella occidentalis and the like;

Hymenoptera:

Formicidae such as Monomorium pharaonis, Vespidae, bethylid wasp,Tenthredinidae such as Athalia japonica, and the like;

Orthoptera:

Gryllotalpidae, Acrididae, and the like;

Aphaniptera:

Ctenocephalides felis, Ctenocephalides canis, Pulex irritans, Xenopsyllacheopis, and the like;

Anoplura:

Pediculus humanus corporis, Phthirus pubis, Haematopinus eurysternus,Dalmalinia ovis, and the like;

Isoptera:

Reticulitermes speratus, Coptotermes formosanus, and the like;

Acarina:

Tetranychidae such as Tetranychus urticae, Panonychus citri, Oligonychusspp., and the like,

Eriophyidae such as Aculops pelekassi and the like,

Tarsonemidae such as Polyphagotarsonemus latus, and the like,

Tenuipalpidae,

Tuckerellidae,

Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava,Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, Boophilusmicroplus, Rhipicephalus sanguineus, and the like,

Acaridae such as Tyrophagus putrescentiae, and the like,

Epidermoptidae such as Dermatophagoides farinae, Dermatophagoidesptrenyssnus, and the like,

Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletusmoorei, and the like,

Dermanyssidae.

The noxious arthropods controlling composition of the present inventioncontains the compound of the present invention and an inert carrier.Generally, it is a preparation obtained by mixing the compound of thepresent invention and a solid carrier, a liquid carrier, a gaseouscarrier and/or bait for poison bait, and if necessary, adding asurfactant and other adjuvant for formulation. The formulation includesan oil solution, an emulsion, a flowable formulation, a wettable powder,a granule, a powder, a microcapsule, and the like. These formulationscan be converted to use into a poison bait, a sheet. In the noxiousarthropods controlling composition of the present invention, thecompound of the present invention is usually contained in an amount of0.01% to 95% by weight.

The solid carrier for formulation includes, for example, a fine powerand a granule of clays (e.g., kaolin clay, diatomite, bentonite,Fubasami clay, acid clay, etc.), synthetic hydrated silicon oxide, talc,ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur,activated carbon, calcium carbonate, hydrated silica) or chemicalfertilizers (e.g., ammonium sulfate, ammonium phosphate, ammoniumnitrate, urea, ammonium chloride).

The liquid carrier for formulation includes, for example, water,alcohols (e.g., methanol, ethanol, isopropyl alcohol, butanol, hexanol,benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol),ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone), aromatichydrocarbons (e.g., toluene, xylene, ethylbenzen, dodecylbenzen,phenylxylylethane, methylnaphthalene), aliphatic hydrocarbons (e.g.,hexane, cyclohexane, kerosine, light oil), esters (e.g., ethyl acetate,butyl acetate, isopropyl mylistate, ethyl oleate, diisopropyl adipate,diisobutyl adipate, propyleneglycol monomethyl ether acetate), nitriles(e.g., acetonitrile, isobutyronitrile), ethers (e.g., diisopropyl ether,1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethylether, diethylene glycol monomethyl ether, propylene glycol monomethylether, dipropylene glycol monomethylether,3-methoxy-3-methyl-1-butanol), acid amides (e.g., N,N-dimethylformamide,N,N-dimethylacetamide), halogenated hydrocarbons (e.g., dichloromethane,trichloroethane, carbontetrachloride), sulfoxides (e.g.,dimethylsulfoxide), and vegetable oils (e.g., soy bean oil, cotton seedoil).

The gaseous carrier for formulation includes, for example,fluorocarbons, butane gas, liquefied petroleum gas (LPG), dimethylether, and carbon dioxide.

The surfactant for formulation includes, for example, non-ionicsurfactant, such as polyoxyethylene alkyl ether, polyoxyethylenealkylaryl ether, polyethyleneglycol fatty acid ester; anionicsurfactant, such as alkylsulfonic acid salts, alkylbenzenesulfonic acidsalts, alkylsurfic acid salts.

The other adjuvant for formulation includes, for example, binders,dispersants and stabilizers, and specifically for example, casein,gelatin, polysaccharides (e.g., starch, gum arabic, cellulosederivatives, alginic acid), lignin derivatives, bentonite, syntheticwater-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone,polyacrylic acid), PAP (isopropyl acid phosphate), BHT(2,6-di-t-butyl-4-methylphenol), BHA (a mixture of2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).

The method for controlling noxious arthropods of the present inventionis applying the compound of the present invention to arthropods directlyand/or habitats of arthropods (e.g., plant, soil, indoor, in-body ofanimals, and so on). The compound of the present invention is usuallyused as the noxious arthropods controlling composition.

When the noxious arthropods controlling composition of the presentinvention is used for a control of arthropods in agriculture andforestry, the application amount is usually 1 to 10,000 g as thecompound of the present invention per 10,000 m². The emulsions, wettablepowders and flowable formulations of the noxious arthropods controllingcomposition of the present invention are usually applied after dilutionwith water to have an active ingredient concentration of 0.01 to 10,000ppm, while powders and granules are usually applied as such.

These preparations and the dilutions of the preparation may be sprayeddirectly to arthropods or the plants to be protected from arthropods.The arthropods living in a soil can be controlled by treating the soilwith these preparations.

Furthermore, the reginous preparations processed to sheets or strip formcan be applied by a method such as winding around plants, stretching inthe vicinity of plants and laying on the soil surface at the plantbottom.

When the noxious arthropods controlling composition of the presentinvention is used for a control of noxious arthropods in indoor (e.g.,fly, mesquite, cockroach), the application amount is usually 0.01 to1,000 mg as the compound of the present invention per 1 m² in case ofapplication for plane surface, and 0.01 to 500 mg as the compound of thepresent invention per 1 m³ in case of application for space. Theemulsions, wettable powders and flowable formulations are usuallyapplied after dilution with water to have an active ingredientconcentration of 0.1 to 1,000 ppm, while oil solutions, aerosols,smoking agents and poison baits are usually applied as such.

The noxious arthropods controlling composition of the present inventioncan contain other noxious arthropods controlling compositions,nematocides, fungicides, herbicides, plant growth regulators,synergists, fertilizers, soil conditioners, animal feeds, and the like.

The active ingredients of noxious arthropods controlling composition andnematocides include, for example, organophosphorus compounds such asFenitrothion, Fenthion, Pyridaphenthion, Diazinon, Chlorpyriphos,Chlorpyriphos-methyl, Acephate, Methidathion, Disulfoton, DDVP,Sulprofos, Cyanophos, Dioxabenzofos, Dimethoate, Phenthoate, Malathion,Trichlorfon, Azinphos-methyl, Monocrotophos Ethion Profenofos,Methyl-parathion, and Isoxathion; carbamate compounds such as BPMC,Benfuracarb, Propoxur, Carbosulfan, Carbaril, Methomyl, Ethiofencarb,Aldicarb, Oxamyl, Fenothiocarb, Thiodicarb, and Alanycarb; pyrethroidcompounds such as Etofenprox, Fenvalerate, Esfenvalerate, Fenpropathrin,Cypermethrin, alfa-Cypermethrin, zeta-Cypermethrin, Permethrin,Cyhalothrin, lambda-Cyhalothrin, delta-Cyhalothrin, Cyfluthrin,beta-Cyfluthrin, Cycloprothrin, Fluvalinate, Flucythrinate, Bifenthrin,Acrinathrin, Traromethrin and Silafluofen; neonicotinoid compounds suchas Acetamiprid, Nitenpyram, Thiamethoxiam and Thialoprid; Nereistoxinderivatives such as Cartap, Thiocyclam, and Bensultap; chlorinatedhydrocarbon compounds such as Endosulfan, gamma-BHC, and1,1-bis(chlorophenyl)-2,2,2-trichloroethanol; benzoylphenylureacompounds such as Chlorfluazuron, Teflubenzuron, Fulphenoxron, andLufenuron; phenylhydrazide compounds such as Tebufenozide,Chromafenozide, Methoxyfenozide and Halofenozide; formamidinederivatives such as Amitraz and Chlordimeform; thiourea derivatives suchas Diafenthiuron; Buprofezin; Chlorfenapyr; Spinosad and derivativesthereof, Emamectin benzoate; Indoxacarb; Pymetrozine; phenylpyrazolederivatives; Bromopropylate; Tetradifon; Chinomethionat; Propargite;Fenbutatin oxide; Cyhexatin; Hexathiazox; Clofentezine; Pyridaben;Fenpyroximate; Tebufenpyrad; Pyrimidifen; Fenazaquin; Bifenazate;Acequinocyl; Spirodiclofen; Spiromesifen; polynactin complexes [e.g.,tetranactin, dinactin, trinactin]; Milbemectin; Avermectin; Azadilactin.

The present invention will be further illustrated by the followingproduction examples, formulation examples, and test examples; however,the present invention is not limited to these examples.

The following describes the production examples for the presentcompounds.

PRODUCTION EXAMPLE 1

200 mg of the compound of formula (i):

was dissolved in 3 ml of N,N-dimethylformamide, 100 mg of potassiumcarbonate and 100 mg of 1,1,3-trichloropropene were added to themixture, and the mixture was stirred at 70° C. for one hour. Thereaction mixture was cooled to room temperature, water and 10%hydrochloric acid were added thereto, and extracted with ethyl acetate.The organic layer was washed with water and saturated brine, dried overmagnesium sulfate, and concentrated under reduced pressure. The residuewas subjected to silica gel column chromatography to obtain 190 mg ofthe compound of formula (1):

(hereinafter, referred as the present compound (1)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 9.51 (1H, s), 6.83-6.97 (8H, m), 6.16 (1H,t), 4.64 (2H, d), 3.66 (3H, s), 2.45 (3H, s)

PRODUCTION EXAMPLE 2

440 mg of the compound of formula (ii):

was dissolved in 5 ml of N,N-dimethylformamide, 220 mg of potassiumcarbonate and 210 mg of 1,1,3-trichloropropene were added to themixture, and the mixture was stirred at 70° C. for one hour. Thereaction mixture was cooled to room temperature, water and 10%hydrochloric acid were added thereto, and extracted with ethyl acetate.The organic layer was washed with water and saturated brine, dried overmagnesium sulfate, and concentrated under reduced pressure. The residuewas subjected to silica gel column chromatography to obtain 480 mg ofthe compound of formula (2):

(hereinafter, referred as the present compound (2)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 9.53 (1H, s), 6.86-6.98 (8H, m), 6.16 (1H,t), 3.66 (3H, s), 2.85 (2H, q), 1.26 (3H, t)

PRODUCTION EXAMPLE 3

200 mg of the present compound (1) was dissolved in 5 ml of pyridine, 45mg of methoxyamine hydrochloric acid salt was added to the mixture underice-cooling, and the mixture was stirred at room temperature for twohours. The reaction mixture was concentrated under reduced pressure.Water and 10% hydrochloric acid were added to the residue, and extractedwith ethyl acetate. The organic layer was washed with water andsaturated brine, dried over magnesium sulfate, and concentrated underreduced pressure. The residue was subjected to silica gel columnchromatography to obtain 200 mg of the compound of formula (3):

(hereinafter, referred as the present compound (3)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.74 (1H, s), 6.16-6.96 (8H, m), 6.16 (1H,t), 4.64 (2H, d), 3.81 (3H, s), 3.62 (3H, s), 2.38 (3H, s)

PRODUCTION EXAMPLE 4

By using 50 mg of ethoxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 170 mg of the compound of formula (4):

(hereinafter, referred as the present compound (4)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.75 (1H, s), 6.83-6.95 (8H, m), 6.15 (1H,t), 4.63 (2H, d), 4.04 (2H, q), 3.61 (3H, s), 2.37 (3H, s), 1.21 (3H, t)

PRODUCTION EXAMPLE 5

By using 62 mg of isopropoxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 140 mg of the compound of formula (5):

(hereinafter, referred as the present compound (5)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.77 (1H, s), 6.82-6.98 (8H, m), 6.15 (1H,t), 5.37 (1H, q), 4.63 (2H, d), 3.61 (3H, s), 2.37 (3H, s), 1.73 (6H, d)

PRODUCTION EXAMPLE 6

By using 248 mg the present compound (1) and 80 mg of tert-butoxyaminehydrochloric acid salt instead of methoxyamine hydrochloric acid saltaccording to Production Example 3 was obtained 270 mg of the compound offormula (6):

(hereinafter, referred as the present compound (6)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.76 (1H, s), 6.82-6.99 (8H, m), 6.16 (1H,t), 4.63 (2H, d), 3.62 (3H, s), 2.38 (3H, s), 1.21 (9H, s)

PRODUCTION EXAMPLE 7

By using 77 mg of pentyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 130 mg of the compound of formula (7):

(hereinafter, referred as the present compound (7)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.76 (1H, s), 6.83-6.95 (8H, m), 6.16 (1H,t), 4.64 (2H, d), 3.98 (2H, t), 3.61 (3H, s), 2.37 (3H, s), 1.58 (2H,br), 1.30-1.32 (5H, m), 0.89 (3H, t)

PRODUCTION EXAMPLE 8

By using 60 mg of 2-propynyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 140 mg of the compound of formula (8):

(hereinafter, referred as the present compound (8)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.80 (1H, s), 6.84-6.96 (8H, m), 6.16 (1H,t), 4.64 (2H, d), 4.60 (1H, s), 3.62 (3H, s), 2.44 (3H, s)

PRODUCTION EXAMPLE 9

By using 55 mg of allyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 200 mg of the compound of formula (9):

(hereinafter, referred as the present compound (9)).

1H-NMR (CDCl₃, TMS) δ (ppm): 7.79 (1H, s), 6.83-6.95 (8H, m), 6.15 (1H,t), 5.90-5.97 (1H, m), 5.16-5.28 (2H, m), 4.64 (2H, d), 4.50 (2H, d),3.61 (3H, s)

PRODUCTION EXAMPLE 10

By using 100 mg of 3,3-dichloro-2-propenyloxyamine hydrochloric acidsalt instead of methoxyamine hydrochloric acid salt according toProduction Example 3 was obtained 130 mg of the compound of formula(10):

(hereinafter, referred as the present compound (10)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.75 (1H, s), 6.83-6.95 (8H, m), 6.15 (1H,t), 6.03 (1H, t), 4.64 (2H, d), 4.57 (2H, d), 3.62 (3H, s), 2.36 (3H, s)

PRODUCTION EXAMPLE 11

By using 75 mg of benzyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 165 mg of the compound of formula (11):

(hereinafter, referred as the present compound (11)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.80 (1H, s), 7.28-7.32 (5H, m), 6.81-6.95(8H, m), 6.16 (1H, t), 5.02 (2H, s), 4.63 (2H, d), 3.60 (3H, s), 2.35(3H, s)

PRODUCTION EXAMPLE 12

By using 55 mg of (E)-2-butenyloxyamine hydrochloric acid salt insteadof methoxyamine hydrochloric acid salt according to Production Example 3was obtained 90 mg of the compound of formula (12):

(hereinafter, referred as the present compound (12)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.77 (1H, s), 6.83-6.96 (8H, m), 6.16 (1H,t), 5.60-6.17 (2H, m), 4.64 (2H, d), 4.42 (2H, d), 3.62 (3H, s), 2.37(3H, q) 1.71 (3H, d)

PRODUCTION EXAMPLE 13

190 mg of the present compound (2) was dissolved in 5 ml of pyridine, 43mg of methoxyamine hydrochloric acid salt was added to the mixture underice-cooling, and the mixture was stirred at room temperature for twohours. The reaction mixture was concentrated under reduced pressure.Water and 10% hydrochloric acid were added to the residue, and extractedwith ethyl acetate. The organic layer was washed with water andsaturated brine, dried over magnesium sulfate, and concentrated underreduced pressure. The residue was subjected to silica gel columnchromatography to obtain 150 mg of the compound of formula (13):

(hereinafter, referred as the present compound (13)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.74 (1H, s), 6.83-6.95 (8H, m), 6.16 (1H,t), 4.64 (2H, d), 3.80 (3H, s), 3.62 (3H, s), 2.78 (2H, q), 1.27 (3H, t)

PRODUCTION EXAMPLE 14

By using 180 mg of the present compound (2) and 50 mg of ethoxyaminehydrochloric acid salt instead of methoxyamine hydrochloric acid saltaccording to Production Example 3 was obtained 160 mg of the compound offormula (14):

(hereinafter, referred as the present compound (14)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.77 (1H, s), 6.83-6.95 (8H, m), 6.16 (1H,t), 4.64 (2H, d), 4.04 (2H, q), 3.62 (3H, s), 2.77 (2H, q), 1.19-1.28(6H, m)

PRODUCTION EXAMPLE 15

190 mg of the compound of formula (iii):

was dissolved in 2 ml of N,N-dimethylformamide, 80 mg of potassiumcarbonate and 80 mg of 1,1,3-trichloropropene were added to the mixture,and the mixture was stirred at 80° C. for one hour. The reaction mixturewas cooled to room temperature, water and 10% hydrochloric acid wereadded thereto, and extracted with ethyl acetate. The organic layer waswashed with water and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 150 mg of the compound of formula(15):

(hereinafter, referred as the present compound (15)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.84 (1H, s), 6.85-6.95 (8H, m), 6.16 (1H,t), 4.64 (2H, d), 3.78 (3H, s), 3.71 (3H, s)

PRODUCTION EXAMPLE 16

170 mg of the compound of the formula (iv):

was dissolved in 3 ml of N,N-dimethylformamide, 80 mg of potassiumcarbonate and 70 mg of 1,3-dichloro-2-butene were added to the mixture,and the mixture was stirred at 80° C. for one hour. The reaction mixturewas cooled to room temperature, water and 10% hydrochloric acid wereadded thereto, and extracted with ethyl acetate. The organic layer waswashed with water and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 160 mg of the compound of formula(16):

(hereinafter, referred as the present compound (16)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.73 (1H, s), 6.82-6.96 (8H, m), 5.76 (1H,t), 4.66 (2H, d), 4.48 (3H, s), 3.61 (3H, s), 2.38 (3H, s), 2.17 (3H, s)

PRODUCTION EXAMPLE 17

By using 60 mg of 1,3-dichloropropene instead of 1,3-dichloro-2-buteneaccording to Production Example 16 was obtained 130 mg of the compoundof formula (17):

(hereinafter, referred as the present compound (17)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.74 (1H, s), 6.83-6.95 (8H, m), 6.37-6.40(1H, m), 6.13-6.19 (1H, m), 4.50 (2H, d), 3.80 (3H, s), 3.61 (3H, s),2.38 (3H, s)

PRODUCTION EXAMPLE 18

114 mg of the present compound (1) was dissolved in 3 ml of pyridine, 25mg of hydroxylamine hydrochloric acid salt was added to the mixtureunder ice-cooling, and the mixture was stirred at room temperature forthirty minutes. The reaction mixture was concentrated under reducedpressure. Water and 10% hydrochloric acid were added to the residue, andextracted with ethyl acetate. The organic layer was washed with waterand saturated brine, dried over magnesium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to obtain 80 mg of the compound of formula (18):

(hereinafter, referred as the present compound (18)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.83 (1H, s), 7.08 (1H, s), 6.84-6.96 (8H,m), 6.16 (1H, t), 4.64 (2H, d), 3.61 (3H, s), 2.36 (3H, s)

PRODUCTION EXAMPLE 19

By using 370 mg of the present compound (1) and 110 mg of propoxyaminehydrochloric acid salt instead of methoxyamine hydrochloric acid saltaccording to Production Example 3 was obtained 400 mg of the compound offormula (19):

(hereinafter, referred as the present compound (19)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 0.90 (3H, t), 1.61 (2H, m), 2.37 (3H, s),3.62 (3H, s), 3.94 (2H, t), 4.64 (2H, d), 6.16 (1H, t), 6.83-6.96 (8H,m), 7.77 (1H, s)

PRODUCTION EXAMPLE 20

By using 150 mg of the present compound (1) and 60 mg ofneopentyloxyamine hydrochloric acid salt instead of methoxyaminehydrochloric acid salt according to Production Example 3 was obtained130 mg of the compound of formula (20):

(hereinafter, referred as the present compound (20)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 0.90 (6H, d), 1.46-1.70 (3H, m), 2.37 (3H,s), 3.61 (3H, s), 4.02 (2H, t), 4.64 (2H, d), 6.16 (1H, t), 6.82-6.96(8H, m), 7.75 (1H, s)

PRODUCTION EXAMPLE 21

By using 150 mg of the present compound (1) and 60 mg of3-methyl-2-butenyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 150 mg of the compound of formula (21):

(hereinafter, referred as the present compound (21)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.70 (3H, s), 1.75 (3H, s), 2.37 (3H, s),3.61 (3H, s), 4.50 (2H, d), 4.63 (2H, d), 5.38 (1H, m), 6.16 (1H, t),6.82-6.96 (8H, m), 7.77 (1H, s)

PRODUCTION EXAMPLE 22

By using 150 mg of the present compound (1) and 50 mg of1-methyl-2-propynyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 110 mg of the compound of formula (22):

(hereinafter, referred as the present compound (22)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.46 (3H, d), 2.38 (3H, s), 2.43 (1H, d),3.62 (3H, s), 4.63 (2H, d), 4.79 (1H, m), 6.16 (1H, t), 6.83-6.96 (8H,m), 7.79 (1H, s)

PRODUCTION EXAMPLE 23

By using 150 mg of the present compound (1) and 50 mg of1-methylpropoxyamine hydrochloric acid salt instead of methoxyaminehydrochloric acid salt according to Production Example 3 was obtained170 mg of the compound of formula (23):

(hereinafter, referred as the present compound (23)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 0.88 (3H, t), 1.15 (3H, d), 1.41-1.64 (2H,m), 2.37 (3H, s), 3.62 (3H, s), 4.04 (1H, m), 4.63 (2H, d), 6.16 (1H, t)6.83-6.96 (8H, m), 7.76 (1H, s)

PRODUCTION EXAMPLE 24

By using 150 mg of the present compound (1) and 70 mg of1,2-dimethylpropoxyamine hydrochloric acid salt instead of methoxyaminehydrochloric acid salt according to Production Example 3 was obtained160 mg of the compound of formula (24):

(hereinafter, referred as the present compound (24)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 0.83 (3H, d), 0.88 (3H, d), 1.11 (3H, d),1.82 (1H, m), 2.37 (3H, s), 3.62 (3H, s), 3.89 (1H, m), 4.64 (2H, d),6.16 (1H, t), 6.82-6.96 (8H, m), 7.76 (1H, s)

PRODUCTION EXAMPLE 25

By using 150 mg of the present compound (1) and 50 mg of2-fluoroethoxyamine hydrochloric acid salt instead of methoxyaminehydrochloric acid salt according to Production Example 3 was obtained130 mg of the compound of formula (25):

(hereinafter, referred as the present compound (25)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.36 (3H, s), 3.62 (3H, s), 4.21 (2H, dt),4.56 (2H, dt), 4.64 (2H, d), 6.16 (1H, t), 6.82-6.97 (8H, m), 7.83 (1H,s)

PRODUCTION EXAMPLE 26

By using 150 mg of the present compound (1) and 70 mg of3,3,3-trifluoropropoxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 140 mg of the compound of formula (26):

(hereinafter, referred as the present compound (26)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.36 (5H, m), 3.63 (3H, s), 4.19 (2H, t),4.64 (2H, d), 6.16 (1H, t), 6.83-6.96 (8H, m), 7.77 (1H, s)

PRODUCTION EXAMPLE 27

By using 150 mg of the present compound (1) and 70 mg of4,4,4-trifluorobutoxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 120 mg of the compound of formula (27):

(hereinafter, referred as the present compound (27)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.86 (2H, m), 2.12 (2H, m), 2.36 (3H, s),3.62 (3H, s), 4.03 (2H, t), 4.64 (2H, d), 6.16 (1H, t), 6.82-6.96 (8H,m) 7.77 (1H, s)

PRODUCTION EXAMPLE 28

By using 150 mg of the present compound (1) and 70 mg of3-chloro-2-propenyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 160 mg of the compound of formula (28):

(hereinafter, referred as the present compound (28)) as the mixture ofdiastereomers.

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.36 (1.5H, s), 2.36 (1.5H, s), 3.62 (3H,s), 4.45 (1H, dd), 4.64 (2H, d), 4.70 (1H, dd), 5.94 (0.5H, m), 6.04(0.5H, m), 6.16 (2H, m), 6.83-6.96 (8H, m), 7.76 (0.5H, s), 7.77 (0.5H,s)

PRODUCTION EXAMPLE 29

By using 150 mg of the present compound (1) and 110 mg of3,3-dibromo-2-propenyloxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 220 mg of the compound of formula (29):

(hereinafter, referred as the present compound (29)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.36 (3H, s), 3.62 (3H, s), 4.48 (2H, d),4.64 (2H, d), 6.16 (1H, t), 6.59 (1H, t), 6.83-6.97 (8H, m), 7.76 (1H,s)

PRODUCTION EXAMPLE 30

By using 150 mg of the present compound (1) and 60 mg of butoxyaminehydrochloric acid salt instead of methoxyamine hydrochloric acid saltaccording to Production Example 3 was obtained 160 mg of the compound offormula (30):

(hereinafter, referred as the present compound (30)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 0.91 (3H, t), 1.35 (2H, m), 1.56 (2H, m),2.37 (3H, s), 3.62 (3H, s), 4.00 (2H, t), 4.64 (2H, d), 6.16 (1H, t),6.82-6.96 (8H, m), 7.76 (1H, s)

PRODUCTION EXAMPLE 31

200 mg of the present compound (18) was dissolved in 2 ml ofN,N-dimethylformamide, 120 mg of potassium carbonate and 110 mg ofbromoacetonitrile were added to the mixture, and the mixture was stirredat 40° C. for five hours. The reaction mixture was cooled to roomtemperature, the reaction mixture added to dilute hydrochloric acid, andextracted with ethyl acetate. The organic layer was washed with waterand saturated brine, dried over magnesium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to obtain 80 mg of the compound of formula (31):

(hereinafter, referred as the present compound (31)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.38 (3H, s), 3.63 (3H, s), 4.63 (4H, m),6.16 (1H, t), 6.85-6.98 (8H, m), 7.82 (1H, s)

PRODUCTION EXAMPLE 32

By using 3.50 g of the present compound (1) and 1.35 g of2,2,2-trifluoroethoxyamine hydrochloric acid salt instead ofmethoxyamine hydrochloric acid salt according to Production Example 3was obtained 3.85 g of the compound of formula (32):

(hereinafter, referred as the present compound (32)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.36 (3H, s), 3.62 (3H, s), 4.34 (2H, q),4.64 (2H, d), 6.16 (1H, t), 6.82-6.97 (8H, m), 7.83 (1H, s)

PRODUCTION EXAMPLE 33

150 mg of the present compound (18) was dissolved in 2 ml ofN,N-dimethylformamide, 90 mg of potassium carbonate and 90 mg of1-bromo-2-methylpropane were added to the mixture, and the mixture wasstirred at 70° C. for ten hours. The reaction mixture was cooled to roomtemperature, the reaction mixture was added to dilute hydrochloric acid,and extracted with ethyl acetate. The organic layer was washed withwater and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 40 mg of the compound of formula(33):

(hereinafter, referred as the present compound (33)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 0.88 (6H, d), 1.90 (1H, m), 2.37 (3H, s),3.62 (3H, s), 3.76 (2H, d), 4.64 (2H, d), 6.16 (1H, t), 6.83-6.96 (8H,m) 7.77 (1H, s)

PRODUCTION EXAMPLE 34

90 mg of sodium hydride (60% oil suspension) was suspended in 5 ml ofhexane, and 460 mg of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehydewas added to the mixture at room temperature. Afterward 500 mg of thecompound of formula (v):

was added dropwise to the mixture under reflux condition, and themixture was stirred five hours under reflux condition. Saturatedammonium chloride aqueous solution was added to the reaction mixture,and extracted with ethyl acetate. The organic layer was washed withdilute hydrochloric acid, water and saturated brine, dried overmagnesium sulfate, and concentrated under reduced pressure. The residuewas subjected to silica gel column chromatography to obtain 260 mg ofthe compound of the formula (34):

(hereinafter, referred as the present compound (34)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.45 (3H, s), 3.65 (3H, s), 4.64 (2H, d),6.15 (1H, t), 6.78-7.01 (7H, m), 9.51 (1H, s)

PRODUCTION EXAMPLE 35

150 mg of the present compound (34) was dissolved in 2 ml of pyridine,40 mg of 2-propynyloxyamine hydrochloric acid salt was added to themixture under ice-cooling, and the mixture was stirred at roomtemperature for five hours. The reaction mixture was concentrated underreduced pressure. Dilute hydrochloric acid were added to the residue,and extracted with ethyl acetate. The organic layer was washed withwater and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 150 mg of the compound of formula(35):

(hereinafter, referred as the present compound (35)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.36 (3H, s), 2.43 (1H, t), 3.62 (3H, s),4.59 (2H, d), 4.63 (2H, d), 6.15 (1H, t), 6.76-7.01 (7H, m), 7.80 (1H,s)

PRODUCTION EXAMPLE 36

200 mg of the present compound (18) was dissolved in 2 ml ofN,N-dimethylformamide, 80 mg of potassium carbonate and 60 mg of2,3-dichloropropene were added to the mixture at room temperature, andthe mixture was stirred at 70° C. for ten hours. The reaction mixturewas cooled to room temperature, added to dilute hydrochloric acid, andextracted with ethyl acetate. The organic layer was washed with waterand saturated brine, dried over magnesium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to obtain 130 mg of the compound of formula (36):

(hereinafter, referred as the present compound (36)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.35 (3H, s), 3.62 (3H, s), 4.52 (2H, s),4.64 (2H, d), 5.33 (1H, s), 5, 35 (1H, s), 6.16 (1H, t), 6.82-6.97 (8H,m), 7.84 (1H, s)

PRODUCTION EXAMPLE 37

200 mg of the present compound (18) was dissolved in 2 ml ofN,N-dimethylformamide, 90 mg of potassium carbonate and 110 mg of2-chloroethyl methansulfonate were added to the mixture at roomtemperature, and the mixture was stirred at 70° C. for ten hours. Thereaction mixture was cooled to room temperature, added to dilutehydrochloric acid, and extracted with ethyl acetate. The organic layerwas washed with water and saturated brine, dried over magnesium sulfate,and concentrated under reduced pressure. The residue was subjected tosilica gel column chromatography to obtain 90 mg of the compound offormula (37):

(hereinafter, referred as the present compound (37)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.35 (3H, s), 3.60 (2H, t), 3.63 (3H, s),4.18 (2H, t), 4.64 (2H, d), 6.16 (1H, t), 6.83-6.98 (8H, m), 7.82 (1H,s)

PRODUCTION EXAMPLE 38

270 mg of the compound of the formula (vi):

was dissolved in 2 ml of N,N-dimethylformamide, 150 mg of potassiumcarbonate and 140 mg of 1,1,3-trichloropropene were added to themixture, and the mixture was stirred at room temperature for ten hours.The reaction mixture was cooled, added to dilute hydrochloric acid, andextracted with ethyl acetate. The organic layer was washed with waterand saturated brine, dried over magnesium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to obtain 350 mg of the compound of formula (38):

(hereinafter, referred as the present compound (38)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.25 (3H, s), 2.47 (3H, s), 3.57 (3H, s),4.64 (2H, d), 6.16 (1H, t), 6.81-6.97 (8H, m)

PRODUCTION EXAMPLE 39

160 mg of the present compound (38) was dissolved in 2 ml of pyridine,50 mg of 2-propynyloxyamine hydrochloric acid salt was added to themixture at room temperature, and the mixture was stirred at roomtemperature for ten hours. The reaction mixture was concentrated underreduced pressure. Dilute hydrochloric acid were added to the residue,and extracted with ethyl acetate. The organic layer was washed withwater and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 170 mg of the compound of formula(39):

(hereinafter, referred as the present compound (39)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.00 (3H, s), 2.39 (3H, s), 2.43 (1H, t),3.58 (3H, s), 4.64 (2H, d), 4.65 (2H, d), 6.16 (1H, t), 6.77-6.97 (8H,m)

PRODUCTION EXAMPLE 40

300 mg of the present compound (18) was dissolved in 3 ml ofN,N-dimethylformamide, 100 mg of potassium carbonate and 110 mg of1-bromo-2-butyne were added to the mixture at room temperature, and themixture was stirred at 40° C. for ten hours. The reaction mixture wascooled to room temperature, added to dilute hydrochloric acid, andextracted with ethyl acetate. The organic layer was washed with waterand saturated brine, dried over magnesium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to obtain 250 mg of the compound of formula (40):

(hereinafter, referred as the present compound (40)).

¹H-NMR (CDCl₃, TMS) δ (ppm): 1.85 (3H, t), 2.37 (3H, s), 3.62 (3H, s),4.57 (2H, q), 4.64 (2H, d), 6.16 (1H, t), 6.83-6.97 (8H, m), 7.79 (1H,s)

Next, the following describes the reference production examples for theintermediates of the present invention

REFERENCE PRODUCTION EXAMPLE 1

330 mg of the compound of formula (i) was dissolved in 3 ml of pyridine,100 mg of methoxyamine hydrochloric acid salt was added thereto atice-cooling, and the mixture was stirred at room temperature for twohours. The reaction mixture was concentrated under reduced pressure.Water and 10% hydrochloric acid were added to the residue, and extractedwith ethyl acetate. The organic layer was washed with water andsaturated brine, dried over magnesium sulfate, and concentrated underreduced pressure. The residue was subjected to silica gel columnchromatography to obtain 290 mg of the compound of formula (iv).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.74 (1H, s), 6.80-6.90 (8H, m), 5.97 (1H,s), 3.81 (3H, s), 3.61 (3H, s), 2.39 (3H, s)

REFERENCE PRODUCTION EXAMPLE 2

240 mg of the compound of formula (vii)

was dissolved in 3 ml of pyridine, 64 mg of methoxyamine hydrochloricacid salt was added thereto at ice-cooling, and the mixture was stirredat room temperature for two hours. The reaction mixture was concentratedunder reduced pressure. Water and 10% hydrochloric acid were added tothe residue, and extracted with ethyl acetate. The organic layer waswashed with water and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 260 mg of the compound of formula(iii).

¹H-NMR (CDCl₃, TMS) δ (ppm): 7.83 (1H, s), 6.79-7.11 (8H, m), 5.28 (1H,br), 3.78 (3H, s), 3.70 (3H, s)

REFERENCE PRODUCTION EXAMPLE 3

300 mg of 4,4′-dihydroxydiphenyl ether was dissolved in 5 ml ofN,N-dimethylformamide, 120 mg of sodium hydride (60% oil suspension) wasadded thereto under ice-cooling, the mixture was stirred at roomtemperature for ten minutes. Afterward, 230 mg of5-chloro-1,3-dimethyl-1H-pyrazole-4-carboaldehyde in 3 ml ofN,N-dimethylformamide was added dropwise at 70° C. under stirring overten minutes, stirred at 70° C. for two hours. The reaction mixture wascooled to room temperature, water and 10% hydrochloric acid were addedthereto, and extracted with ethyl acetate. The organic layer was washedwith water and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 260 mg of the compound of formula(i).

¹H-NMR (CDCl₃, TMS) δ (ppm): 9.50 (1H, s), 6.76-6.99 (8H, m), 5.44 (1H,br), 3.66 (3H, s), 2.45 (3H, s)

REFERENCE PRODUCTION EXAMPLE 4

500 mg of 4,4′-dihydroxydiphenyl ether was dissolved in 5 ml ofN,N-dimethylformamide, 200 mg of sodium hydride (60% oil suspension) wasadded thereto under ice-cooling, the mixture was stirred at roomtemperature for ten minutes. Afterward, 410 mg of5-chloro-3-ethyl-1-methyl-1H-pyrazole-4-carboaldehyde in 5 ml ofN,N-dimethylformamide was added dropwise at 70° C. under stirring overten minutes, stirred at 70° C. for two hours. The reaction mixture wascooled to room temperature, water and 10% hydrochloric acid were addedthereto, and extracted with ethyl acetate. The organic layer was washedwith water and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 460 mg of the compound of formula(ii).

¹H-NMR (CDCl₃, TMS) δ (ppm): 9.51 (1H, s), 6.79-6.94 (8H, m), 5.44 (1H,s), 3.66 (3H, s), 2.86 (2H, q), 1.27 (3H, t)

REFERENCE PRODUCTION EXAMPLE 5

570 mg of 4,4′-dihydroxydiphenyl ether was dissolved in 5 ml ofN,N-dimethylformamide, 170 mg of sodium hydride (60% oil suspension) wasadded thereto under ice-cooling, the mixture was stirred at roomtemperature for ten minutes. Afterward, 570 mg of5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde in 5 mlof N,N-dimethylformamide was added dropwise at 70° C. under stirringover ten minutes, stirred at 70° C. for two hours. The reaction mixturewas cooled to room temperature, water and 10% hydrochloric acid wereadded thereto, and extracted with ethyl acetate. The organic layer waswashed with water and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 440 mg of the compound of formula(vii).

1H-NMR (CDCl₃, TMS) δ (ppm): 9.66 (1H, s), 6.79-6.93 (8H, m), 4.95 (1H,s), 3.81 (3H, s)

REFERENCE PRODUCTION EXAMPLE 6

560 mg of 4,4′-dihydroxydiphenyl ether was dissolved in 10 ml ofN,N-dimethylformamide, 140 mg of sodium hydride (60% oil suspension) wasadded thereto under ice-cooling, the mixture was stirred at 70° C. forone hour. Afterward, 400 mg of1-(5-chloro-1,3-dimethyl-1H-pyrazo-4-yl)ethanone in 5 ml ofN,N-dimethylformamide was added dropwise at 70° C. under stirring overfifteen minutes, stirred at 70° C. for six hours. The reaction mixturewas cooled to room temperature, diluted hydrochloric acid was addedthereto, and extracted with ethyl acetate. The organic layer was washedwith water and saturated brine, dried over magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to obtain 340 mg of the compound of formula(vi).

¹H-NMR (CDCl₃, TMS) δ (ppm): 2.26 (3H, s), 2.47 (3H, s), 3.57 (3H, s),5.22 (1H, s), 6.79-6.95 (8H, m)

The following describes formulation examples wherein parts representparts by weight.

FORMULATION EXAMPLE 1

10 parts of each of the present compounds (1) to (40) is dissolved inthe mixture of 35 parts of xylene and 35 parts of N,N-dimethylformamide,and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts ofcalcium dodecylbenzenesulfonate are added thereto, followed by wellstirring and mixing, to give 10% emulsion for each compound.

FORMULATION EXAMPLE 2

20 parts of each of the present compounds (1) to (40) is added to amixture containing 4 parts of sodium laurylsulfate, 2 parts of calciumlignin sulfonate, 20 parts of synthetic hydrated silicone oxide finepowder, and 54 parts of diatomaceous earth, followed by well stirringand mixing, to give 20% wettable powder for each compound.

FORMULATION EXAMPLE 3

To 2 parts of each of the present compounds (1) to (40) are added 1 partof synthetic hydrated silicon oxide fine powder, 2 parts of calciumlignin sulfonate, 30 parts of bentonite, and 65 parts of kaolin clay,followed by well stirring and mixing, and an appropriate amount of wateris added to this mixture, followed by further stirring, granulation witha granulator, and air drying, to give 2% granule for each compound.

FORMULATION EXAMPLE 4

1 part of each of the present compounds (1) to (40) is dissolved in anappropriate amount of acetone, and 5 parts of synthetic hydrated siliconoxide fine powder, 0.3 part of PAP, and 93.7 parts of Fubasami clay arewell stirring and mixing, and acetone is removed by evaporation from themixture, to give 1% powder for each compound.

FORMULATION EXAMPLE 5

10 parts of each of the present compounds (1) to (40), 35 parts of whitecarbon containing 50 parts of polyoxyethylene alkyl ether sulfateammonium salt, and 55 parts of water are mixed and pulverized by the wetgrinding method to give 10% flowable formulation for each compound.

FORMULATION EXAMPLE 6

0.1 part of each of the present compounds (1) to (40) is dissolved in amixture of 5 parts of xylene and 5 parts of trichloroethane, and theresulting solution is mixed with 89.9 parts of deodorized kerosine togive 0.1% oil solution for each compound.

FORMULATION EXAMPLE 7

10 mg of each of the present compounds (1) to (40) is dissolved in 0.5ml of acetone, the solution is applied to 5 g of powdery solid animalfood (powdery solid animal food for bleeding CE-2; a product of CLEAJapan, Inc.) and mixed uniformly, and acetone is removed by evaporationfrom the mixture, to give poison bait for each compound.

The following test example will demonstrate the noxious arthropodscontrolling activity of the compound of the present invention.

TEST EXAMPLE 1

Each of the present compounds (2) to (15), (17) to (33), (36) to (40)and the comparative compound described below was formulated according toFormulation Example 5, and each formulations was diluted with water sothat the concentration of the present compound or the comparativecompound came to 500 ppm.

About twenty female adults of Tetranychus urticae were set free on brushbean (Phaseolus vulgaris) in the primary leaf stage, which had beenpotted in a plastic cup for 7 days after the seeding. After 1 day, a 30ml of the diluted formulation described-above was sprayed over theplant. On the 8th and 13th day after the application, the numbers oflived Tetranychus urticae on the leaf of brush bean plant were examined,and the Controlling Rates were calculated by the following scheme.Controlling Rate=100×{1−(a number of lived Tetranychus urticae in thetreatment)/(a number of lived Tetranychus urticae in the non-treatment)}

As the result, in the treatment of the present compound (2) to (15),(17) to (33), and (36) to (40), all of the Controlling rates were notless than 90% on 8th day and 13th day after the application. In thetreatment of the comparative compound, the Controlling rate was lessthan 30% on 8th day and 13th day after the application.

Comparative Compound

which is disclosed as the Compound No. 189 in the Japan unexaminedPatent Publication S63-183564, p. 21.

TEST EXAMPLE 2

Each of the present compounds (3), (4), (6) to (10), (12) to (33), (36),(37), (39) and (40) was formulated according to Formulation Example 5,and each formulation was diluted with water so that the concentration ofthe present compound came to 500 ppm.

On the bottom of a polyethylene cup having a diameter of 5.5 cm, 9 g ofa artificial bait (Silkmate 2S; produced by Nosan Corporation) was laid,and 1 ml of the diluted formulation described-above was added dropwiseon the artificial bait. Thirty first-instar larvae of Adoxophyes oranawere set free in the polyethylene cup. After 7 days, the numbers of thesurviving Adoxophyes orana were examined to obtain the rate of deadpests.

As the result, in the treatment of the present compound (3), (4), (6) to(10), (12) to (33), (36), (37), (39) and (40), all of the rate of deadpests were not less than 90%.

INDUSTRIAL APPLICABILITY

By using the compound of the present invention, noxious arthropods canbe controlled.

1. A pyrazole compound of formula (a):

wherein R¹ represents C1-C4 alkyl or trifluoromethyl, R² representsC1-C4 alkyl, R³ represents hydrogen or C1-C6 alkyl; R⁴ representshalogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl or C1-C3 haloalkoxy,m represents 0 to 4 integer, each of R⁴s is same or different when m is2 to 4 integer; R⁵ represents halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3haloalkyl or C1-C3 haloalkoxy, n represents 0 to 4 integer, each of R⁵sis same or different when n is 2 to 4 integer; R⁶ and R⁷ are same ordifferent and represents hydrogen, halogen or methyl, X representsoxygen or R⁸O—N; R⁸ represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl,C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl,C2-C5 cyanoalkyl or benzyl (wherein the benzyl may be substituted withhalogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl,trifluoromethyl or trifluoro methoxy).
 2. The pyrazole compoundaccording to claim 1, wherein R³ is hydrogen in the formula (a).
 3. Thepyrazole compound according to claim 1, wherein R³ is C1-C6 alkyl in theformula (a).
 4. The pyrazole compound according to any one of claims 1to 3, wherein X is R⁸O—N, and R⁸ is hydrogen, C1-C6 alkyl, C1-C6haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6haloalkynyl, C2-C5 cyanoalkyl or benzyl (wherein the benzyl may besubstituted with halogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C5alkoxycarbonyl, trifluoromethyl or trifluoro methoxy) in the formula(a).
 5. The pyrazole compound according to any one of claims 1 to 3,wherein X is R⁸O—N, and R⁸ is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl,C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl orC2-C5 cyanoalkyl in the formula (a).
 6. The pyrazole compound accordingto any one of claims 1 to 3, wherein X is R⁸O—N, and R⁸ is a benzyl(wherein the benzyl may be substituted with halogen, C1-C4 alkyl, C1-C4alkoxy, C2-C5 alkoxycarbonyl, trifluoromethyl or trifluoro methoxy) inthe formula (a).
 7. The pyrazole compound according to any one of claims1 to 3, wherein X is oxygen in the formula (a).
 8. The pyrazole compoundaccording to claim 1, wherein R⁶ is halogen in the formula (a).
 9. Thepyrazole compound according to claim 1, wherein R⁶ and R⁷ are halogen inthe formula (a).
 10. The pyrazole compound according to claim 1, whereinR⁶ and R⁷ are chlorine in the formula (a).
 11. The pyrazole compoundaccording to claim 1, wherein R⁴ and R⁵ are halogen, C1-C3 alkyl, C1-C3alkoxy or trifluoromethyl, and m and n is 0 to 2 integer in the formula(a).
 12. A noxious arthropods controlling composition comprising aneffective amount of the pyrazole compound according to claim
 1. 13. Amethod for controlling noxious arthropods comprising applying aneffective amount of the pyrazole compound according to claim 1 tonoxious arthropods or habitat of noxious arthropods.
 14. A compound offormula (b):

wherein R¹ represents C1-C4 alkyl or trifluoromethyl, R² representsC1-C4 alkyl, R³ represents hydrogen or C1-C6 alkyl; R⁴ representshalogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl or C1-C3 haloalkoxy,m represents 0 to 4 integer, each of R⁴s is same or different when m is2 to 4 integer; R⁵ represents halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3haloalkyl or C1-C3 haloalkoxy, n represents 0 to 4 integer, each of R⁵sis same or different when n is 2 to 4 integer; X represents oxygen orR⁸O—N; R⁸ represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C2-C5cyano alkyl or benzyl (wherein the benzyl may be substituted withhalogen, C1-C4 alkyl, C1-C4 alkoxy, C2-C5 alkoxycarbonyl,trifluoromethyl or trifluoro methoxy).